Tricyclic benzoylcyclohexanedione derivatives

ABSTRACT

Tricyclic benzoylcyclohexanedione derivatives of the formula I                    
     where X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , and m are defined herein, and their agriculturally useful salts. Process for preparing the tricyclic benzoylcyclohexanedione derivatives; compositions comprising them and the use of these derivatives or of the compositions comprising them for controlling undesirable plants are described.

This application is a 371 of PCT/EP 00/04806 filed May 26, 2000, now WO00/73311, Dec. 7, 2000.

The present invention relates to novel tricyclic benzoylcyclohexanedionederivatives of the formula I

where:

X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;

Y together with the two carbons to which it is attached forms asaturated, partially saturated or unsaturated 5- or 6-memberedheterocycle which contains one to three identical or differentheteroatoms selected from the following group: oxygen, sulfur ornitrogen;

R¹,R²,R⁶,R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R⁴ is hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl,N,N-di-(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino,N—(C₁-C₆-haloalkylsulfonyl)amino,N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino orN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;

R⁵ is hydrogen, C₁-C₆-alkyl or halogen;

R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl,formyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl;

m is 0, 1 or 2;

R⁹ is a radical IIa or IIb

 where:

R¹⁰ is hydroxyl, mercapto, halogen, OR¹⁷, SR¹⁷, SOR¹⁸, SO₂R¹⁸, OSO₂R¹⁸,NR¹⁹R²⁰ or N-bonded heterocyclyl which may be partially or fullyhalogenated and/or may carry one to three of the following radicals:nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

R¹¹, R¹⁵ are hydrogen, C₁-C₄-alkyl or C₁-C₄-alkoxycarbonyl;

R¹², R¹⁴, R¹⁶ are hydrogen or C₁-C₄-alkyl;

R¹³ is hydrogen, halogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,di-(C₁-C₆-alkoxy)methyl, (C₁-C₆-alkoxy)-(C₁-C₆-alkylthio)methyl,di-(C₁-C₆-alkylthio)methyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl;

is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the sixlast-mentioned radicals may be substituted by one to three C₁-C₄-alkylradicals; or

R¹² and R¹³ or R¹³ and R¹⁶ together form a π-bond or a C₁-C₅-alkyl chainwhich may carry one to three radicals from the following group: halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; or

R¹² and R¹⁶ together form a C₁-C₄-alkyl chain which may carry one tothree radicals from the following group: halogen, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; or

R¹³ and R¹⁴ together form a —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S—,—S—(CH₂)_(p)—S—, —O—(CH₂)_(q)— or —S—(CH₂)_(q)— chain which may besubstituted by one to three radicals from the following group: halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; or

R¹³ and R¹⁴ together with the carbon to which they are attached form acarbonyl group;

R¹⁷ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₂₀-alkylcarbonyl,C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl,C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,di-(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, wherethe alkyl, cycloalkyl or alkoxy radicals mentioned may be partially orfully halogenated and/or may carry one to three of the following groups:cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl,C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl,phenylaminocarbonyl, N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl,phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonylor heterocyclyl-C₁-C₆-alkenylcarbonyl, where the phenyl or theheterocyclyl radical of the 18 last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹⁷ [sic] is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl orC₃-C₆-cycloalkyl, where the four radicals mentioned may be partially orfully halogenated and/or may carry one to three of the following groups:cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl orC₁-C₄-haloalkoxycarbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl,where the phenyl or the heterocyclyl radical of the four last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino,C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino,where the alkyl, cycloalkyl or alkoxy radicals mentioned may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: cyano, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl orC₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl,heterocycly-C₁-C₄-alkyl [sic] or heterocyclylcarbonyl, where the phenylor heterocyclyl radical of the six last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²⁰ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

p is 2, 3 or 4;

q is 1, 2, 3, 4 or 5;

and their agriculturally useful salts.

Moreover, the invention relates to processes for preparing compounds ofthe formula I, to compositions comprising them and to the use of thesederivatives or of the compositions comprising them for controllingharmful plants.

WO 97/19087 and EP-A 860 441 disclose tricyclic compounds which arecharacterized in that the benzoyl unit that they contain in each case isfused to a bicycle via positions 3 and 4. However, the herbicidalproperties of the prior-art compounds and their compatibility with cropplants are not entirely satisfactory.

It is an object of the present invention to provide novel biological, inparticular herbicidally active, compounds having improved properties.

We have found that this object is achieved by the tricyclicbenzoylcyclohexanedione derivatives of the formula I and theirherbicidal action.

Furthermore, we have found processes for synthesizing the compounds ofthe formula I. We have also found herbicidal compositions which comprisethe compounds I and have very good herbicidal action. Moreover, we havefound processes for preparing these compositions and methods forcontrolling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more chiral centers, in which case they are presentas enantiomers or diastereomer mixtures. The invention provides both thepure enantiomers or diestereomers and their mixtures.

The compounds of the formula I can also be present in the form of theiragriculturally useful salts, the type of salt usually being immaterial.In general, the salts of those cations and the acid addition salts ofthose acids are suitable whose cations and anions, respectively, do notadversely affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium or potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, where,if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl) sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

In the case of R¹⁰=hydroxyl or mercapto, IIa also represents thetautomeric forms IIa′, IIa″ and IIa′″

and IIb also represents the tautomeric forms IIb′, IIb″ and IIb′″.

The organic molecular moieties mentioned for the substituents R¹-R²⁰ oras radicals on phenyl and heterocyclyl radicals, and all other radicalslisted in this application, are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,i.e. all alkyl, haloalkyl, hydroxyalkyl, di(alkoxy)methyl,(alkoxy)(alkylthio)methyl, di(alkylthio)methyl, alkoxy-, haloalkoxy-,alkylthio-, haloalkylthio-, alkylsulfinyl, haloalkylsulfinyl-,alkylsulfonyl-, haloalkylsulfonyl-, N-alkylaminosulfonyl,N,N-dialkylaminosulfonyl, trialkylsulfonium, trialkylsulfoxonium,N-alkylamino, N,N-dialkylamino, alkylcarbonylamino,N-alkylsulfonylamino, N-haloalkylsulfonylamino,N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino,alkylcarbonyl-, alkoxycarbonyl-, haloalkyoxycarbonyl [sic],alkylthiocarbonyl, alkylcarbonyloxy-, alkylaminocarbonyl-,dialkylaminocarbonyl-, dialkylaminothiocarbonyl, alkoxyalkyl-,hydroxyalkoxyalkyl, alkoxyiminoalkyl, phenylalkenylcarbonyl,heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl-,N-alkyl-N-phenylaminocarbonyl-, N-alkyl-N-heterocyclylaminocarbonyl-,phenylalkyl-, heterocyclylalkyl-, phenylcarbonylalkyl-,heterocyclylcarbonylalkyl-, alkoxyalkoxycarbonyl-, alkenylcarbonyl-,alkenyloxycarbonyl-, alkenylaminocarbonyl-,N-alkenyl-N-alkylaminocarbonyl-, N-alkenyl-N-alkoxyaminocarbonyl-,alkynylcarbonyl-, alkynyloxycarbonyl-, alkynylaminocarbonyl-,N-alkynyl-N-alkylaminocarbonyl-, N-alkynyl-N-alkoxyaminocarbonyl-,alkenyl-, alkynyl-, haloalkenyl-, haloalkynyl-, alkenyloxy andalkynyloxy moieties may be straight-chain or branched. Unless indicatedotherwise, halogenated substituents preferably carry one to fiveidentical or different halogen atoms. The term halogen represents ineach case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl and the alkyl moieties of hydroxy-C₁-C₄-alkyl,tri-(C₁-C₄-alkyl)sulfonium and tri-(C₁-C₄-alkyl)sulfoxonium: for examplemethyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkoxyimino-C₁-C₆-alkyl,N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl, N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl,phenyl-C₁-C₆-alkyl, N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)-amino,N—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino,heterocyclyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, andalso, for example, phenyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutylor nonafluorobutyl;

C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above, and also, forexample, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,6-iodohexyl or dodecafluorohexyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy,butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;

C₁-C₆-alkoxy, and the alkoxy moieties of di-(C₁-C₆-alkoxy)-methyl,(C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl andN—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: C₁-C₄-alkoxy asmentioned above, and also, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy,2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy or nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above, and, for example,5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy,6-iodohexoxy or dodecafluorohexoxy;

C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio,1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or1,1-dimethylethylthio;

C₁-C₆-alkylthio, and the alkylthio moieties of(C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl, di(C₁-C₆-alkylthio)methyl andC₁-C₆-alkylthiocarbonyl: C₁-C₄-alkylthio as mentioned above, and also,for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or1-ethyl-2-methylpropylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e. for example, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio,2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio;

C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthioo [sic] as mentioned above, andalso, for example, 5-fluoropentylthio, 5-chloropentylthio,5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio,6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthioor dodecafluorohexylthio;

C₁-C₆-alkylsulfinyl (C₁-C₆-alkyl-S(═O)—): for example methylsulfinyl,ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl,1-methylpropylsulfinyl, 2-methylpropylsulfinyl,1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;

C₁-C₆-haloalkylsulfinyl: C₁-C₆-alkylsulfinyl radical as mentioned abovewhich is partially or fully substituted by fluorine, chlorine, bromineand/or iodine, i.e., for example, fluoromethylsulfinyl,difluoromethylsulfinyl, trifluoromethylsulfinyl,chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl,2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl,2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl,heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl,1-(chloromethyl)-2-chloroethylsulfinyl,1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, nonafluorobutylsulfinyl,5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl,5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl,6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl ordodecafluorohexylsulfinyl;

C₁-C₆-alkylsulfonyl (C₁-C₆-alkyl-S(═O)₂—), and the alkylsulfonylradicals of N—(C₁-C₆-alkylsulfonyl)amino andN—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino: for examplemethylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl,butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl,1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;

C₁-C₆-haloalkylsulfonyl, and the haloalkylsulfonyl radicals ofN—(C₁-C₆-haloalkylsulfonyl)amino andN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino: a C₁-C₆-alkylsulfonylradical as mentioned above which is partially or fully substituted byfluorine, chlorine, bromine and/or iodine, i.e., for example,fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl,chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl,3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(chloromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl,5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl,5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl,6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;

C₁-C₆-alkylamino: for example, methylamino, ethylamino, propylamino,1-methylethylamino, butylamino, 1-methylpropylamino,2-methylpropylamino, 1,1-dimethylethylamino, pentylamino,1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino,2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino,1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino,2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino,2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino,1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino,1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or1-ethyl-2-methylpropylamino;

(C₁-C₆-alkylamino)sulfonyl: for example methylaminosulfonyl,ethylaminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl,butylaminosulfonyl, 1-methylpropylaminosulfonyl,2-methylpropylaminosulfonyl, 1,1-dimethylethylaminosulfonyl,pentylaminosulfonyl, 1-methylbutylaminosulfonyl,2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl,2,2-dimethylpropylaminosulfonyl, 1-ethylpropylaminosulfonyl,hexylaminosulfonyl, 1,1-dimethylpropylaminosulfonyl,1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl,2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl,4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl,1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl,2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl,3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl,2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl,1,2,2-trimethylpropylaminosulfonyl, 1-ethyl-1-methylpropylaminosulfonylor 1-ethyl-2-methylpropylaminosulfonyl;

di(C₁-C₆-alkyl)aminosulfonyl: for example N,N-dimethylaminosulfonyl,N,N-diethylaminosulfonyl, N,N-di(1-methylethyl)aminosulfonyl,N,N-dipropylaminosulfonyl, N,N-dibutylaminosulfonyl,N,N-di(1-methylpropyl)aminosulfonyl,N,N-di(2-methylpropyl)aminosulfonyl,N,N-di(1,1-dimethylethyl)aminosulfonyl, N-ethyl-N-methylaminosulfonyl,N-methyl-N-propylaminosulfonyl, N-methyl-N-(1-methylethyl)aminosulfonyl,N-butyl-N-methylaminosulfonyl, N-methyl-N-(1-methylpropyl)aminosulfonyl,N-methyl-N-(2-methylpropyl)aminosulfonyl,N-(1,1-dimethylethyl)-N-methylaminosulfonyl,N-ethyl-N-propylaminosulfonyl, N-ethyl-N-(1-methylethyl)aminosulfonyl,N-butyl-N-ethylaminosulfonyl, N-ethyl-N-(1-methylpropyl)aminosulfonyl,N-ethyl-N-(2-methylpropyl)aminosulfonyl,N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl,N-(1-methylethyl)-N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl,N-(1-methylpropyl)-N-propylaminosulfonyl,N-(2-methylpropyl)-N-propylaminosulfonyl,N-(1,1-dimethylethyl)-N-propylaminosulfonyl,N-butyl-N-(1-methylethyl)aminosulfonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl,N-butyl-N-(1-methylpropyl)aminosulfonyl,N-butyl-N-(2-methylpropyl)aminosulfonyl,N-butyl-N-(1,1-dimethylethyl)aminosulfonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl,N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl,N-methyl-N-pentylaminosulfonyl, N-methyl-N-(1-methylbutyl)aminosulfonyl,N-methyl-N-(2-methylbutyl)aminosulfonyl,N-methyl-N-(3-methylbutyl)aminosulfonyl,N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl,N-methyl-N-(1-ethylpropyl)aminosulfonyl, N-methyl-N-hexylaminosulfonyl,N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl,N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl,N-methyl-N-(1-methylpentyl)aminosulfonyl,N-methyl-N-(2-methylpentyl)aminosulfonyl,N-methyl-N-(3-methylpentyl)aminosulfonyl,N-methyl-N-(4-methylpentyl)aminosulfonyl,N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl,N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl,N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl,N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl,N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl,N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl,N-methyl-N-(1-ethylbutyl)aminosulfonyl,N-methyl-N-(2-ethylbutyl)aminosulfonyl,N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,N-Methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,N-ethyl-N-pentylaminosulfonyl, N-ethyl-N-(1-methylbutyl)aminosulfonyl,N-ethyl-N-(2-methylbutyl)aminosulfonyl,N-ethyl-N-(3-methylbutyl)aminosulfonyl,N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl,N-ethyl-N-(1-ethylpropyl)aminosulfonyl, N-ethyl-N-hexylaminosulfonyl,N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl,N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl,N-ethyl-N-(1-methylpentyl)aminosulfonyl,N-ethyl-N-(2-methylpentyl)aminosulfonyl,N-ethyl-N-(3-methylpentyl)aminosulfonyl,N-ethyl-N-(4-methylpentyl)aminosulfonyl,N-ethyl-N-(1,1-dimethylbutyl)aminosulfonyl,N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl,N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl,N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl,N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl,N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl,N-ethyl-N-(1-ethylbutyl)aminosulfonyl,N-ethyl-N-(2-ethylbutyl)aminosulfonyl,N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl,N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl,N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl orN,N-dihexylaminosulfonyl;

di(C₁-C₄-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino,N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino,N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino,N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino,N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino,N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino,N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino,N-(1-methylethyl)-N-(1-methylpropyl)amino,N-(1-methylethyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,N-butyl-N-(1,1-dimethylethyl)amino,N-(1-methylpropyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino orN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;

di(C₁-C₆-alkyl)amino: a di(C₁-C₄-alkyl)amino as mentioned above, andalso N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino,N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;

C₁-C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl,propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,1-methylpropylcarbonyl, 2-methylpropylcarbonyl or1,1-dimethylethylcarbonyl;

C₁-C₆-alkylcarbonyl, and the alkylcarbonyl radicals ofC₁-C₆-alkylcarbonylamino: C₁-C₄-alkylcarbonyl as mentioned above, andalso, for example, pentylcarbonyl, 1-methylbutylcarbonyl,2-methylbutylcarbonyl, 3-methylbutylcarbonyl,2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl,1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl,4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl,1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl,2,2,-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl,3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;

C₁-C₂₀-alkylcarbonyl: C₁-C₆-alkylcarbonyl as mentioned above, and alsoheptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;

C₁-C₄-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl,1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or1,1-dimethylethoxycarbonyl;

(C₁-C₆-alkoxy)carbonyl: (C₁-C₄-alkoxy)carbonyl as mentioned above, andalso, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl;

C₁-C₄-haloalkoxycarbonyl: a C₁-C₄-alkoxycarbonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethoxycarbonyl,difluoromethoxycarbonyl, trifluoromethoxycarbonyl,chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl,2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,2-chloro-2,2-difluoroethoxycarbonyl,2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl,pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl,3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl,3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl,heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl,1-(chloromethyl)-2-chloroethoxycarbonyl,1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl ornonafluorobutoxycarbonyl;

C₁-C₆-haloalkoxycarbonyl: C₁-C₄-haloalkoxycarbonyl as mentioned above,and also 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl,5-bromopentoxycarbonyl, 5-iodopentoxycarbonyl, 6-fluorohexoxycarbonyl,6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl ordodecafluorohexoxycarbonyl;

(C₁-C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy,1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or1,1-dimethylethylcarbonyloxy;

(C₁-C₄-alkylamino)carbonyl: for example methylaminocarbonyl,ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl,butylaminocarbonyl, 1-methylpropylaminocarbonyl,2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;

(C₁-C₆-alkylamino)carbonyl: (C₁-C₄-alkylamino)carbonyl as mentionedabove, and also, for example, pentylaminocarbonyl,1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,1-ethylpropylaminocarbonyl, hexylaminocarbonyl,1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl,1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl,3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl,1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl,1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl,2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl,1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl,1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl,1-ethyl-1-methylpropylaminocarbonyl or1-ethyl-2-methylpropylaminocarbonyl;

di(C₁-C₄-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl,N,N-diethylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl,N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl,N,N-di(1-methylpropyl)aminocarbonyl,N,N-di(2-methylpropyl)aminocarbonyl,N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl,N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl,N-methyl-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-methylaminocarbonyl,N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl) aminocarbonyl,N-ethyl-N-(2-methylpropyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N-(1-methylpropyl)-N-propylaminocarbonyl,N-(2-methylpropyl)-N-propylaminocarbonyl,N-(1,1-dimethylethyl)-N-propylaminocarbonyl,N-butyl-N-(1-methylethyl)aminocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,N-butyl-N-(1-methylpropyl)aminocarbonyl,N-butyl-N-(2-methylpropyl)aminocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl orN-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;

di(C₁-C₆-alkyl)aminocarbonyl: di(C₁-C₄-alkyl)aminocarbonyl as mentionedabove, and also, for example, N-methyl-N-pentylaminocarbonyl,N-methyl-N-(1-methylbutyl)aminocarbonyl,N-methyl-N-(2-methylbutyl)aminocarbonyl,N-methyl-N-(3-methylbutyl)aminocarbonyl,N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl,N-methyl-N—(1,1-dimethylpropyl)aminocarbonyl,N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,N-methyl-N-(1-methylpentyl)aminocarbonyl,N-methyl-N-(2-methylpentyl)aminocarbonyl,N-methyl-N-(3-methylpentyl)aminocarbonyl,N-methyl-N-(4-methylpentyl)aminocarbonyl,N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,N-methyl-N-(1-ethylbutyl)aminocarbonyl,N-methyl-N-(2-ethylbutyl)aminocarbonyl,N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl,N-ethyl-N-(2-methylbutyl)aminocarbonyl, N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl,N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl,N-ethyl-N-(4-methylpentyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl,N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,N-ethyl-N-(3,3-dimethylbutyl)-aminocarbonyl,N-ethyl-N-(1-ethylbutyl)aminocarbonyl,N-ethyl-N-(2-ethylbutyl)aminocarbonyl,N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl,N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl orN,N-dihexylaminocarbonyl;

di(C₁-C₆-alkyl)aminothiocarbonyl: for exampleN,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,N,N-di(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl,N,N-dibutylaminothiocarbonyl, N,N-di(1-methylpropyl)aminothiocarbonyl,N,N-di(2-methylpropyl)aminothiocarbonyl,N,N-di(1,1-dimethylethyl)aminothiocarbonyl,N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl,N-methyl-N-(1-methylethyl)aminothiocarbonyl,N-butyl-N-methylaminothiocarbonyl,N-methyl-N-(1-methylpropyl)aminothiocarbonyl,N-methyl-N-(2-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,N-ethyl-N-propylaminothiocarbonyl,N-ethyl-N-(1-methylethyl)aminothiocarbonyl,N-butyl-N-ethylaminothiocarbonyl,N-ethyl-N-(1-methylpropyl)aminothiocarbonyl,N-ethyl-N-(2-methylpropyl)aminothiocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl,N-(1-methylethyl)-N-propylaminothiocarbonyl,N-butyl-N-propylaminothiocarbonyl,N-(1-methylpropyl)-N-propylaminothiocarbonyl,N-(2-methylpropyl)-N-propylaminothiocarbonyl,N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,N-butyl-N-(1-methylethyl)aminothiocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,N-butyl-N-(1-methylpropyl)aminothiocarbonyl,N-butyl-N-(2-methylpropyl)aminothiocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,N-methyl-N-pentylaminothiocarbonyl,N-methyl-N-(1-methylbutyl)aminothiocarbonyl,N-methyl-N-(2-methylbutyl)aminothiocarbonyl,N-methyl-N-(3-methylbutyl)aminothiocarbonyl,N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,N-methyl-N-hexylaminothiocarbonyl,N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,N-methyl-N-(1-methylpentyl)aminothiocarbonyl,N-methyl-N-(2-methylpentyl)aminothiocarbonyl,N-methyl-N-(3-methylpentyl)aminothiocarbonyl,N-methyl-N-(4-methylpentyl)aminothiocarbonyl,N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,N-ethyl-N-pentylaminothiocarbonyl,N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,N-ethyl-N-hexylaminothiocarbonyl,N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl,N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl,N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl,N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl orN,N-dihexylaminothiocarbonyl;

C₁-C₄-alkoxy-C₁-C₄-alkyl and the alkoxyalkyl moieties ofhydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl, which is substituted byC₁-C₄-alkoxy as mentioned above, i.e., for example, methoxymethyl,ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl,(1-methylpropoxy)methyl, (2-methylpropoxy)methyl,(1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl,2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl,2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl,3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl,3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or4-(1,1-dimethylethoxy)butyl;

C₁-C₄-alkoxy-C₁-C₄-alkoxy as alkoxyalkoxy moieties ofC₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl: C₁-C₄-alkoxy which is substituted byC₁-C₄-alkoxy as mentioned above, i.e., for example, methoxymethoxy,ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy,(1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy,(1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy,2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy,2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy,2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy,2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy,3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy,2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy,2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy,3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy,4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy,4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or4-(1,1-dimethylethoxy)butoxy;

C₃-C₆-alkenyl, and the alkenyl moieties of C₃-C₆-alkenylcarbonyl,C₃-C₆-alkenyloxy, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkenylaminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆)alkylaminocarbonyl [sic] andN—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for exampleprop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl,2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl,2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl,hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl,2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl,1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl,1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl,2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkenyl, and the alkenyl moieties of C₂-C₆-alkenylcarbonyl,phenyl-C₂-C₆-alkenylcarbonyl and heterocyclyl-C₂-C₆-alkenylcarbonyl:C₃-C₆-alkenyl as mentioned above, and also ethenyl;

C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, 2-chloroallyl, 3-chloroallyl,2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl,2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl,3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;

C₃-C₆-alkynyl, and the alkynyl moiety of C₃-C₆-alkynylcarbonyl,C₃-C₆-alkynyloxy, C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylaminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl andN—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for example propargyl,but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl,pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl,pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl,hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl,hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl,hex-3-yn-1-hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-ylor 4-methylpent-2-yn-5-yl;

C₂-C₆-alkynyl, and the alkynyl moieties of C₂-C₆-alkynylcarbonyl:C₃-C₆-alkynyl as mentioned above, and also ethynyl;

C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e. for example, 1,1-difluoroprop-2-yn-1-yl,3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

C₃-C₆-cycloalkyl, and the cycloalkyl moieties ofC₃-C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl;

heterocyclyl, and the heterocyclyl moieties of heterocyclylcarbonyl,heterocyclyl-C₁-C₆-alkyl, heterocyclyloxycarbonyl,heterocyclyloxythiocarbonyl, heterocyclyl-C₂-C₆-alkenylcarbonyl,heterocyclylcarbonyl-C₁-C₆-alkyl,N—(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,heterocyclylaminocarbonyl: a saturated, partially saturated orunsaturated 5- or 6-membered, C-bonded heterocyclic ring containing oneto four identical or different heteroatoms selected from the followinggroup: oxygen, sulfur or nitrogen, i.e., for example, 5-membered ringshaving, for example, one heteroatom, having two heteroatoms, havingthree heteroatoms or having four heteroatoms or, for example, 6-memberedrings having, for example, one heteroatom, having two heteroatoms,having three heteroatoms or having four heteroatoms, i.e. 5-memberedrings having one heteroatom such as:

tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl,tetrahydrothien-3-yl,tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl,2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl,2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl,2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl,2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl,2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl,4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl,3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl,3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl,3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;

5-membered rings having two heteroatoms such as:

tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl,tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl,1,2-Oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl,tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl,1,2-dithiolan-3-yl, 1,2-Dithiolan-4-yl, tetrahydroimidazol-2-yl,tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl,tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl,tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl,1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl,1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl,4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl,2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl,2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl,4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl,2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl,2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl,4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl,2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl,2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl,2,3-dihydroisothiazol-5-yl, Δ³-1,2-dithiol-3-yl, Δ³-1,2-dithiol-4-yl,Δ³-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl,4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl,2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl,2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl,2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl,4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl,2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl,4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl,2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl,1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl,1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl,oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl orthiazol-5-yl;

5-membered rings having three heteroatoms such as:

1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl,1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl,1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl,1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl,1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl,1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl,1,2,3-Δ²-thiadiazolin-4-yl, 1,2,3-Δ²-thiadiazolin-5-yl,1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl,1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl,1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl,1,3,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl,1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl,1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl,1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl,1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-2-yl, 1,2,4-triazolin-3-yl,3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl,2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl,1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or1,2,4-triazol-3-yl;

5-membered rings having four heteroatoms such as:

tetrazol-5-yl;

6-membered rings having one heteroatom such as:

tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl,piperidin-2-yl, piperidin-3-yl, piperidin-4-yl,tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl,2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl,2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl,2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl,2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl,2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl,1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl,1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl,2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl,2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl,2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl,2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl,2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl,1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl,1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl,1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl,2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl,2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl,4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl,4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl,1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl,2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl,2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl,2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl,1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl,1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl,3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl,3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl,3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl,2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl,2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl,2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl,2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl,2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl;

6-membered rings having two heteroatoms such as:

1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl,1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl,1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl,1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl,1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl,hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl,hexahydropyridazin-3-yl, hexahydropyridazin-4-yl,tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl,tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl,tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl,tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl,tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl,tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl,tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl,tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl,2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl,2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl,2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl,2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl,4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl,4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl,4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl,4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl,2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl,2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl,2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl,2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl,2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl,2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl,2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl,2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl,2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl,2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl,3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl,1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl,1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl,1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl,4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl,4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl,4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl,4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl,3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl,3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl,1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl,1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl,1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl,2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl,2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl,2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl,2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl,2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl,4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl,4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl,4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl,6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl,6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl,2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl,2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl,2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl,4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl,4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl,4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl,6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl,6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl,2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl,2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl,2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl,4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl,1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl,1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl,1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl,1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl,1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl,1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl,1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl,3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;

6-membered rings having three heteroatoms such as:

1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl;

6-membered rings having four heteroatoms such as:

1,2,4,5-tetrazin-3-yl;

where, if appropriate, the sulfur of the heterocycles mentioned may beoxidized to S═O or S(═O)₂

and where a bicyclic ring system may be formed with a fused-on phenylring or with a C₃-C₆-carbocycle or with a further 5- to 6-memberedheterocycle;

N-bonded heterocyclyl: a saturated, partially saturated or unsaturated5- or 6-membered N-bonded heterocyclic ring which contains at least onenitrogen and optionally one to three identical or different heteroatomsselected from the following group: oxygen, sulfur or nitrogen, i.e., forexample,

N-bonded 5-membered rings such as:

tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl,2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl,tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl,tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl,4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl,2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl,2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl,2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl,2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl,2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl,imidazol-1-yl, 1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl,1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl,1,2,4-Δ⁵-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl,1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl,1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-1-yl,1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl,1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl,tetrazol-1-yl;

and N-bonded 6-membered rings such as:

piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl,1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl,1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl,hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl,tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl,tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl,2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl,2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl,2H-3,4-dihydro-1,2-oxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl,2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl,1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl,3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl,1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl,2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl,4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl,1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl,1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl;

and also N-bonded cyclic imides such as:

phthalimide, tetrahydrophthalimide, succinimide, maleinimide,glutarimide, 5-oxotriazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl or2,4-dioxo-(1H,3H)-pyrimidin-3-yl;

where a bicyclic ring system may be formed with a fused-on phenyl ringor with a C₃-C₆-carbocycle or a further 5- to 6-membered heterocycle.

All phenyl rings or heterocyclyl radicals and all phenyl components inphenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl,phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,phenylaminocarbonyl and N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl orheterocyclyl components in heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl,heterocyclyloxycarbonyl, heterocyclylaminocarbonyl andN—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl are, unless statedotherwise, preferably unsubstituted or carry one to three halogen atomsand/or one nitro group, one cyano radical and/or one or two methyl,trifluoromethyl, methoxy or trifluoromethoxy substituents.

Furthermore, the expression “Y together with the two carbons to which itis attached forms a saturated, partially saturated or unsaturatedheterocycle which contains one to three identical or differentheteroatoms selected from the following group: oxygen, sulfur ornitrogen” represents, for example, 5-membered rings having oneheteroatom, such as:

tetrahydrofurandiyl, tetrahydrothienediyl, tetrahydropyrroldiyl,dihydrofurandiyl, dihydrothienediyl, dihydropyrroldiyl, furandiyl,thienediyl or pyrroldiyl;

or 5-membered rings having two heteroatoms, such as:

tetrahydropyrazoldiyl, tetrahydroisoxazoldiyl, 1,2-oxathiolanediyl,tetrahydroisothiazoldiyl, 1,2-dithiolanediyl, tetrahydroimidazoldiyl,tetrahydrooxazoldiyl, tetrahydrothiazoldiyl, 1,3-dioxolanediyl,1,3-oxathiolanediyl, dihydropyrazoldiyl, dihydroisoxazoldiyl,dihydroisothiazoldiyl, 1,2-dithioldiyl, dihydroimidazoldiyl,dihydrooxazoldiyl, dihydrothiazoldiyl, dioxoldiyl, oxathioldiyl,pyrazoldiyl, isoxazoldiyl, isothiazoldiyl, imidazoldiyl, oxazoldiyl orthiazoldiyl;

or 5-membered rings having three heteroatoms, such as:

1,2,3-oxadiazolinediyl, 1,2,3-thiadiazolinediyl, 1,2,3-triazolinediyl,1,2,3-oxadiazoldiyl, 1,2,3-thiadiazoldiyl or 1,2,3-triazoldiyl;

or 6-membered rings having one heteroatom, such as:

tetrahydropyrandiyl, piperidinediyl, tetrahydrothiopyrandiyl,dihydropyrandiyl, dihydrothiopyrandiyl, tetrahydropyrindinediyl [sic],pyrandiyl, thiopyrandiyl, dihydropyrinediyl [sic] or pyridinediyl;

or 6-membered rings having two heteroatoms, such as:

1,3-dioxanediyl, 1,4-dioxanediyl, 1,3-dithianediyl, 1,4-dithianediyl,1,3-oxathianediyl, 1,4-oxathianediyl, 1,2-dithianediyl,hexahydropyrimidinediyl, hexahydropyrazinediyl, hexahydropyridazinediyl,tetrahydro-1,3-oxazinediyl, tetrahydro-1,3-thiazinediyl,tetrahydro-1,4-oxazinediyl, tetrahydro-1,2-oxazinediyl,dihydro-1,2-oxazinediyl, dihydro-1,2-thiazinediyl,tetrahydropyridazinediyl, dihydro-1,3-oxazinediyl,dihydro-1,3-oxazinediyl, dihydro-1,3-thiazinediyl,tetrahydropyrimidinediyl, tetrahydropyrazinediyl,dihydro-1,4-thiazinediyl, dihydro-1,4-oxazinediyl,dihydro-1,4-dioxinediyl, dihydro-1,4-dithiinediyl, 1,2-oxazinediyl,1,2-thiazinediyl, 1,3-oxazinediyl, 1,3-thiazinediyl, 1,4-oxazinediyl,1,4-thiazinediyl, dihydropyridazinediyl, dihydropyrazinediyl,dihydropyrimidinediyl, pyridazinediyl, pyrimidinediyl or pyrazinediyl;

or 6-membered rings having 3 heteroatoms, such as:

1,2,4-triazinediyl;

where, if appropriate, the sulfur of the heterocycles mentioned may beoxidized to S═O or S(═O)₂;

and where the radical is fused to the skeleton via two adjacent carbons.

The compounds of the formula I according to the invention where R⁹=IIaare referred to as compounds of the formula Ia, and compounds of theformula I where R⁹=IIb are referred to as Ib.

With respect to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, in each case on their own or in combination:

X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;

Y together with the two carbons to which it is attached forms asaturated, partially saturated or unsaturated 5- or 6-memberedheterocycle which contains one to two identical or different heteroatomsselected from the following group: oxygen, sulfur or nitrogen;

R¹,R² are hydrogen or C₁-C₆-alkyl;

R³ is halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy;

R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl,N,N-di-(C₁-C₆-alkyl)aminosulfonyl, N—( (C₁-C₆-alkylsulfonyl)amino [sic],N—(C₁-C₆-haloalkylsulfony)amino [sic],N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino orN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino; in particular nitro,halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl orC₁-C₆-haloalkylsulfonyl;

R⁵ is hydrogen;

R⁶,R⁷ are hydrogen or C₁-C₆-alkyl;

R⁸ is C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulfonyl;

m is 0, 1 or 2;

R⁹ is a radical IIa

 where

R¹⁰ is hydroxyl, mercapto, halogen, OR¹⁷, SR¹⁷, SO₂R¹⁸, OSO₂R¹⁸, NR¹⁹R²⁰or N-bonded heterocyclyl which may be partially or fully halogenatedand/or may carry one to three of the following radicals: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹¹, R¹⁵ are hydrogen or C₁-C₄-alkyl, such as methyl, ethyl or propyl;preferably hydrogen or methyl;

R¹², R¹⁴, R¹⁶ are hydrogen or C₁-C₄-alkyl, such as methyl, ethyl orpropyl; preferably hydrogen or methyl;

R¹³ is hydrogen, hydroxyl, C₁-C₆-alkyl, di-(C₁-C₆-alkoxy)methyl,(C₁-C₆-alkoxy)-(C₁-C₆-alkylthio)methyl, di-(C₁-C₆-alkylthio)methyl,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl;

is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl,1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the sixlast-mentioned radicals may be substituted by one to three C₁-C₄-alkylradicals;

is preferably hydrogen, hydroxyl or C₁-C₄-alkyl, such as methyl, ethylor propyl; or

R¹² and R¹³ or R¹³ and R¹⁶ together form a πbond or a C₃-C₅-alkyl chainwhich may carry one to three radicals from the following group: halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; or

R¹¹ and R¹⁶ together form a C₁-C₄-alkyl chain which may carry one tothree radicals from the following group: halogen, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; or

R¹³ and R¹⁴ together form a —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S— or—S—(CH₂)_(p)—S— chain which may be substituted by one to three radicalsfrom the following group: halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkylor C₁-C₄-alkoxycarbonyl;

R¹³ and R¹⁴ together preferably form a —O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S—or —S—(CH₂)_(p)—S— chain which may be substituted by one to threeradicals from the following groups: C₁-C₄-alkyl or C₁-C₄-alkoxycarbonyl;or

R¹³ and R¹⁴ together with carbon to which they are attached form acarbonyl group;

R¹⁷ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,C₁-C₂₀-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₃-C₆-cycloalkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl,C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C_(3-C)₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,di-(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, wherethe alkyl, cycloalkyl or alkoxy radicals mentioned may be partially orfully halogenated and/or may carry one to three of the following groups:cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, hydroxycarbonyl,C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl,phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl orheterocyclyl-C₁-C₆-alkenylcarbonyl, where the phenyl or the heterocyclylradical of the 14 last-mentioned substituents may be partially or fullyhalogenated and/or may carry one to three of the following radicals:nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

is preferably C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl orN,N-di(C₁-C₆-alkyl)aminocarbonyl, where the alkyl or alkoxy radicalsmentioned may be partially or fully halogenated and/or may carry one tothree of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio orC₁-C₄-alkoxycarbonyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl,phenylcarbonyl, phenoxycarbonyl, heterocyclyl-[sic],heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl,heterocyclylcarbonyl or heterocyclyloxycarbonyl, where the phenyl or theheterocyclyl radical of the 10 last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹⁸ is C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-cycloalkyl, where the threeradicals mentioned may be partially or fully halogenated and/or maycarry one to three of the following groups: cyano, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl,where the phenyl or the heterocyclyl radical of the four last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹⁹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or di-(C₁-C₆-alkyl)amino, where thealkyl, cycloalkyl or alkoxy radicals mentioned may be partially or fullyhalogenated and/or may carry one to three of the following radicals:cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl,di-(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl,heterocycly-C₁-C₄-alkyl [sic] or heterocyclylcarbonyl, where the phenylor heterocyclyl radical of the six last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²⁰ is C₁-C₆-alkyl or C₃-C₆-alkenyl;

p is 2, 3 or 4.

Particular preference is given to the compounds of the formula I wherethe variables have the meanings below, in each case on their own or incombination:

X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷ or a bond;

Y together with the two carbons to which it is attached forms thefollowing heterocycles:

(in the diagrams of the heterocycles below, the upper wavy line in eachcase represents the linkage to the carbon which carries the radicals R¹and R², and the lower wavy lines represents the linkage to themetacarbon of the benzoyl moiety).

 where the sulfur of the heterocycles mentioned may be oxidized to S═Oor S(═O)₂;

in particular, Y together with the two carbons to which it is attachedforms the heterocycles below:

R¹,R² are hydrogen;

R³ is C₁-C₆-alkyl, such as methyl, ethyl or n-propyl; in particularmethyl;

R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in particular nitro, halogen,such as fluorine, chlorine or bromine, C₁-C₆-haloalkyl such astrifluoromethyl, C₁-C₆-alkylthio such as methylthio or ethylthio orC₁-C₆-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl;particularly preferably nitro, chlorine, trifluoromethyl, methylthio ormethylsulfonyl;

R⁵ is hydrogen;

R⁶,R⁷ are hydrogen or C₁-C₆-alkyl, such as methyl or ethyl; inparticular hydrogen or methyl;

m is 0, 1 or 2; in particular 0 or 1;

R⁹ is a radical IIa

R¹⁰ is hydroxyl, mercapto, OR¹⁷, SR¹⁷ or NR¹⁹R²⁰

Particular preference is given to the compounds Ia where

X is oxygen, sulfur, S(═O)₂, CH₂ or a bond;

Y together with the two carbons to which it is attached forms thefollowing heterocycles:

R¹,R² are hydrogen;

R³ is C₁-C₄-alkyl;

R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl;

R⁵ is hydrogen or C₁-C₆-alkyl;

m is 0, 1 or 2.

Very particular preference is given to the compounds of the formula Ia,where

R¹⁰ is hydroxyl.

Likewise, very particular preference is given to the compounds of theformula I where

R¹⁰ is halogen, OR¹⁷, SR¹⁷, SO₂R¹⁸, OSO₂R¹⁸, NR¹⁹R²⁰ or N-bondedheterocyclyl which may be partially or fully halogenated and/or maycarry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

Likewise, very particular preference is given to the compounds of theformula Ia where

R¹¹, R¹⁵ are hydrogen or C₁-C₄-alkyl;

R¹², R¹⁴, R¹⁶ are hydrogen or C₁-C₄-alkyl;

R¹³ is hydrogen, hydroxyl, C₁-C₆-alkyl, di-(C₁-C₆-alkoxy)-methyl,(C₁-C₆-alkoxy)-(C₁-C₆-alkylthio)methyl, di-(C₁-C₆-alkylthio)methyl,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl orC₁-C₆-haloalkylsulfonyl; in particular hydrogen, hydroxyl orC₁-C₆-alkyl; or

R¹² and R¹⁶ together form a C₁-C₄-alkyl chain which may carry one tothree radicals from the following group: halogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl;

in particular, R¹² and R¹⁶ together form a methylene bridge which maycarry one or two radicals from the following group: halogen, C₁-C₂-alkylor C₁-C₂-haloalkyl; or

R¹³ and R¹⁴ together with the carbons to which they are attached form acarbonyl group.

Likewise, very particular preference is given to the compounds of theformula I where

R¹¹, R¹⁵ are hydrogen or C₁-C₄-alkyl;

R¹², R¹⁴, R¹⁶ are hydrogen or C₁-C₄-alkyl;

R¹³ is hydrogen, hydroxyl, C₁-C₆-alkyl, di-(C₁-C₆-alkoxy)-methyl,(C₁-C₆-alkoxy)(C₁-C₆-alkylthio)methyl, di-(C₁-C₆-alkylthio)methyl,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl orC₁-C₆-haloalkylsulfonyl; in particular hydrogen, hydroxyl orC₁-C₆-alkyl; or

R¹³ and R¹⁴ together with the carbon to which they are attached form acarbonyl group.

Likewise, particular preference is given to the compounds of the formulaI where R⁹ has the following meaning:

Likewise, particular preference is given to the compounds of the formulaIa1 (≡where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=O [sic], the heterocycle isas defined in the structural formula), in particular to the compoundsIal.n where the variables X, R⁴ and R¹⁰ are as defined in Table 1.

The given radical definitions R¹ to R¹⁶, X, Y and m and the meaning ofthe fused heterocycle are of particular importance for the compoundsaccording to the invention not only in combination with one another, butalso on their own.

(For reasons of a clearer presentation, the meaning of the fusedheterocycles in each of the formulae Ia1, Ia2 . . . is in each case asstated in the corresponding structural formula.)

TABLE 1 Ia1

n X R⁴ R¹⁰ 1. Bond F OH 2. Bond Cl OH 3. Bond Br OH 4. Bond NO₂ OH 5.Bond SCH₃ OH 6. Bond SO₂CH₃ OH 7. Bond SO₂CH₂CH₃ OH 8. Bond CH₃ OH 9.Bond CF₃ OH 10. Bond OCHF₂ OH 11. CH₂ F OH 12. CH₂ Cl OH 13. CH₂ Br OH14. CH₂ NO₂ OH 15. CH₂ SCH₃ OH 16. CH₂ SO₂CH₃ OH 17. CH₂ SO₂CH₂CH₃ OH18. CH₂ CH₃ OH 19. CH₂ CF₃ OH 20. CH₂ OCHF₂ OH 21. O F OH 22. O Cl OH23. O Br OH 24. O NO₂ OH 25. O SCH₃ OH 26. O SO₂CH₃ OH 27. O SO₂CH₂CH₃OH 28. O CH₃ OH 29. O CF₃ OH 30. O OCHF₂ OH 31. S F OH 32. S Cl OH 33. SBr OH 34. S NO₂ OH 35. S SCH₃ OH 36. S SO₂CH₃ OH 37. S SO₂CH₂CH₃ OH 38.S CH₃ OH 39. S CF₃ OH 40. S OCHF₂ OH 41. SO₂ F OH 42. SO₂ Cl OH 43. SO₂Br OH 44. SO₂ NO₂ OH 45. SO₂ SCH₃ OH 46. SO₂ SO₂CH₃ OH 47. SO₂ SO₂CH₂CH₃OH 48. SO₂ CH₃ OH 49. SO₂ CF₃ OH 50. SO₂ OCHF₂ OH 51. Bond F OCOC₆H₅ 52.Bond Cl OCOC₆H₅ 53. Bond Br OCOC₆H₅ 54. Bond NO₂ OCOC₆H₅ 55. Bond SCH₃OCOC₆H₅ 56. Bond SO₂CH₃ OCOC₆H₅ 57. Bond SO₂CH₂CH₃ OCOC₆H₅ 58. Bond CH₃OCOC₆H₅ 59. Bond CF₃ OCOC₆H₅ 60. Bond OCHF₂ OCOC₆H₅ 61. CH₂ F OCOC₆H₅62. CH₂ Cl OCOC₆H₅ 63. CH₂ Br OCOC₆H₅ 64. CH₂ NO₂ OCOC₆H₅ 65. CH₂ SCH₃OCOC₆H₅ 66. CH₂ SO₂CH₃ OCOC₆H₅ 67. CH₂ SO₂CH₂CH₃ OCOC₆H₅ 68. CH₂ CH₃OCOC₆H₅ 69. CH₂ CF₃ OCOC₆H₅ 70. CH₂ OCHF₂ OCOC₆H₅ 71. O F OCOC₆H₅ 72. OCl OCOC₆H₅ 73. O Br OCOC₆H₅ 74. O NO₂ OCOC₆H₅ 75. O SCH₃ OCOC₆H₅ 76. OSO₂CH₃ OCOC₆H₅ 77. O SO₂CH₂CH₃ OCOC₆H₅ 78. O CH₃ OCOC₆H₅ 79. O CF₃OCOC₆H₅ 80. O OCHF₂ OCOC₆H₅ 81. S F OCOC₆H₅ 82. S Cl OCOC₆H₅ 83. S BrOCOC₆H₅ 84. S NO₂ OCOC₆H₅ 85. S SCH₃ OCOC₆H₅ 86. S SO₂CH₃ OCOC₆H₅ 87. SSO₂CH₂CH₃ OCOC₆H₅ 88. S CH₃ OCOC₆H₅ 89. S CF₃ OCOC₆H₅ 90. S OCHF₂OCOC₆H₅ 91. SO₂ F OCOC₆H₅ 92. SO₂ Cl OCOC₆H₅ 93. SO₂ Br OCOC₆H₅ 94. SO₂NO₂ OCOC₆H₅ 95. SO₂ SCH₃ OCOC₆H₅ 96. SO₂ SO₂CH₃ OCOC₆H₅ 97. SO₂SO₂CH₂CH₃ OCOC₆H₅ 98. SO₂ CH₃ OCOC₆H₅ 99. SO₂ CF₃ OCOC₆H₅ 100. SO₂ OCHF₂OCOC₆H₅ 101. Bond F OCOC(CH₃)₃ 102. Bond Cl OCOC(CH₃)₃ 103. Bond BrOCOC(CH₃)₃ 104. Bond NO₂ OCOC(CH₃)₃ 105. Bond SCH₃ OCOC(CH₃)₃ 106. BondSO₂CH₃ OCOC(CH₃)₃ 107. Bond SO₂CH₂CH₃ OCOC(CH₃)₃ 108. Bond CH₃OCOC(CH₃)₃ 109. Bond CF₃ OCOC(CH₃)₃ 110. Bond OCHF₂ OCOC(CH₃)₃ 111. CH₂F OCOC(CH₃)₃ 112. CH₂ Cl OCOC(CH₃)₃ 113. CH₂ Br OCOC(CH₃)₃ 114. CH₂ NO₂OCOC(CH₃)₃ 115. CH₂ SCH₃ OCOC(CH₃)₃ 116. CH₂ SO₂CH₃ OCOC(CH₃)₃ 117. CH₂SO₂CH₂CH₃ OCOC(CH₃)₃ 118. CH₂ CH₃ OCOC(CH₃)₃ 119. CH₂ CF₃ OCOC(CH₃)₃120. CH₂ OCHF₂ OCOC(CH₃)₃ 121. O F OCOC(CH₃)₃ 122. O Cl OCOC(CH₃)₃ 123.O Br OCOC(CH₃)₃ 124. O NO₂ OCOC(CH₃)₃ 125. O SCH₃ OCOC(CH₃)₃ 126. OSO₂CH₃ OCOC(CH₃)₃ 127. O SO₂CH₂CH₃ OCOC(CH₃)₃ 128. O CH₃ OCOC(CH₃)₃ 129.O CF₃ OCOC(CH₃)₃ 130. O OCHF₂ OCOC(CH₃)₃ 131. S F OCOC(CH₃)₃ 132. S ClOCOC(CH₃)₃ 133. S Br OCOC(CH₃)₃ 134. S NO₂ OCOC(CH₃)₃ 135. S SCH₃OCOC(CH₃)₃ 136. S SO₂CH₃ OCOC(CH₃)₃ 137. S SO₂CH₂CH₃ OCOC(CH₃)₃ 138. SCH₃ OCOC(CH₃)₃ 139. S CF₃ OCOC(CH₃)₃ 140. S OCHF₂ OCOC(CH₃)₃ 141. SO₂ FOCOC(CH₃)₃ 142. SO₂ Cl OCOC(CH₃)₃ 143. SO₂ Br OCOC(CH₃)₃ 144. SO₂ NO₂OCOC(CH₃)₃ 145. SO₂ SCH₃ OCOC(CH₃)₃ 146. SO₂ SO₂CH₃ OCOC(CH₃)₃ 147. SO₂SO₂CH₂CH₃ OCOC(CH₃)₃ 148. SO₂ CH₃ OCOC(CH₃)₃ 149. SO₂ CF₃ OCOC(CH₃)₃150. SO₂ OCHF₂ OCOC(CH₃)₃ 151. Bond F OCOSCH₃ 152. Bond Cl OCOSCH₃ 153.Bond Br OCOSCH₃ 154. Bond NO₂ OCOSCH₃ 155. Bond SCH₃ OCOSCH₃ 156. BondSO₂CH₃ OCOSCH₃ 157. Bond SO₂CH₂CH₃ OCOSCH₃ 158. Bond CH₃ OCOSCH₃ 159.Bond CF₃ OCOSCH₃ 160. Bond OCHF₂ OCOSCH₃ 161. CH₂ F OCOSCH₃ 162. CH₂ ClOCOSCH₃ 163. CH₂ Br OCOSCH₃ 164. CH₂ NO₂ OCOSCH₃ 165. CH₂ SCH₃ OCOSCH₃166. CH₂ SO₂CH₃ OCOSCH₃ 167. CH₂ SO₂CH₂CH₃ OCOSCH₃ 168. CH₂ CH₃ OCOSCH₃169. CH₂ CF₃ OCOSCH₃ 170. CH₂ OCHF₂ OCOSCH₃ 171. O F OCOSCH₃ 172. O ClOCOSCH₃ 173. O Br OCOSCH₃ 174. O NO₂ OCOSCH₃ 175. O SCH₃ OCOSCH₃ 176. OSO₂CH₃ OCOSCH₃ 177. O SO₂CH₂CH₃ OCOSCH₃ 178. O CH₃ OCOSCH₃ 179. O CF₃OCOSCH₃ 180. O OCHF₂ OCOSCH₃ 181. S F OCOSCH₃ 182. S Cl OCOSCH₃ 183. SBr OCOSCH₃ 184. S NO₂ OCOSCH₃ 185. S SCH₃ OCOSCH₃ 186. S SO₂CH₃ OCOSCH₃187. S SO₂CH₂CH₃ OCOSCH₃ 188. S CH₃ OCOSCH₃ 189. S CF₃ OCOSCH₃ 190. SOCHF₂ OCOSCH₃ 191. SO₂ F OCOSCH₃ 192. SO₂ Cl OCOSCH₃ 193. SO₂ Br OCOSCH₃194. SO₂ NO₂ OCOSCH₃ 195. SO₂ SCH₃ OCOSCH₃ 196. SO₂ SO₂CH₃ OCOSCH₃ 197.SO₂ SO₂CH₂CH₃ OCOSCH₃ 198. SO₂ CH₃ OCOSCH₃ 199. SO₂ CF₃ OCOSCH₃ 200. SO₂OCHF₂ OCOSCH₃ 201. Bond F OCH₃ 202. Bond Cl OCH₃ 203. Bond Br OCH₃ 204.Bond NO₂ OCH₃ 205. Bond SCH₃ OCH₃ 206. Bond SO₂CH₃ OCH₃ 207. BondSO₂CH₂CH₃ OCH₃ 208. Bond CH₃ OCH₃ 209. Bond CF₃ OCH₃ 210. Bond OCHF₂OCH₃ 211. CH₂ F OCH₃ 212. CH₂ Cl OCH₃ 213. CH₂ Br OCH₃ 214. CH₂ NO₂ OCH₃215. CH₂ SCH₃ OCH₃ 216. CH₂ SO₂CH₃ OCH₃ 217. CH₂ SO₂CH₂CH₃ OCH₃ 218. CH₂CH₃ OCH₃ 219. CH₂ CF₃ OCH₃ 220. CH₂ OCHF₂ OCH₃ 221. O F OCH₃ 222. O ClOCH₃ 223. O Br OCH₃ 224. O NO₂ OCH₃ 225. O SCH₃ OCH₃ 226. O SO₂CH₃ OCH₃227. O SO₂CH₂CH₃ OCH₃ 228. O CH₃ OCH₃ 229. O CF₃ OCH₃ 230. O OCHF₂ OCH₃231. S F OCH₃ 232. S Cl OCH₃ 233. S Br OCH₃ 234. S NO₂ OCH₃ 235. S SCH₃OCH₃ 236. S SO₂CH₃ OCH₃ 237. S SO₂CH₂CH₃ OCH₃ 238. S CH₃ OCH₃ 239. S CF₃OCH₃ 240. S OCHF₂ OCH₃ 241. SO₂ F OCH₃ 242. SO₂ Cl OCH₃ 243. SO₂ Br OCH₃244. SO₂ NO₂ OCH₃ 245. SO₂ SCH₃ OCH₃ 246. SO₂ SO₂CH₃ OCH₃ 247. SO₂SO₂CH₂CH₃ OCH₃ 248. SO₂ CH₃ OCH₃ 249. SO₂ CF₃ OCH₃ 250. SO₂ OCHF₂ OCH₃251. Bond F OCH(CH₃)₂ 252. Bond Cl OCH(CH₃)₂ 253. Bond Br OCH(CH₃)₂ 254.Bond NO₂ OCH(CH₃)₂ 255. Bond SCH₃ OCH(CH₃)₂ 256. Bond SO₂CH₃ OCH(CH₃)₂257. Bond SO₂CH₂CH₃ OCH(CH₃)₂ 258. Bond CH₃ OCH(CH₃)₂ 259. Bond CF₃OCH(CH₃)₂ 260. Bond OCHF₂ OCH(CH₃)₂ 261. CH₂ F OCH(CH₃)₂ 262. CH₂ ClOCH(CH₃)₂ 263. CH₂ Br OCH(CH₃)₂ 264. CH₂ NO₂ OCH(CH₃)₂ 265. CH₂ SCH₃OCH(CH₃)₂ 266. CH₂ SO₂CH₃ OCH(CH₃)₂ 267. CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ 268.CH₂ CH₃ OCH(CH₃)₂ 269. CH₂ CF₃ OCH(CH₃)₂ 270. CH₂ OCHF₂ OCH(CH₃)₂ 271. OF OCH(CH₃)₂ 272. O Cl OCH(CH₃)₂ 273. O Br OCH(CH₃)₂ 274. O NO₂ OCH(CH₃)₂275. O SCH₃ OCH(CH₃)₂ 276. O SO₂CH₃ OCH(CH₃)₂ 277. O SO₂CH₂CH₃ OCH(CH₃)₂278. O CH₃ OCH(CH₃)₂ 279. O CF₃ OCH(CH₃)₂ 280. O OCHF₂ OCH(CH₃)₂ 281. SF OCH(CH₃)₂ 282. S Cl OCH(CH₃)₂ 283. S Br OCH(CH₃)₂ 284. S NO₂ OCH(CH₃)₂285. S SCH₃ OCH(CH₃)₂ 286. S SO₂CH₃ OCH(CH₃)₂ 287. S SO₂CH₂CH₃ OCH(CH₃)₂288. S CH₃ OCH(CH₃)₂ 289. S CF₃ OCH(CH₃)₂ 290. S OCHF₂ OCH(CH₃)₂ 291.SO₂ F OCH(CH₃)₂ 292. SO₂ Cl OCH(CH₃)₂ 293. SO₂ Br OCH(CH₃)₂ 294. SO₂ NO₂OCH(CH₃)₂ 295. SO₂ SCH₃ OCH(CH₃)₂ 296. SO₂ SO₂CH₃ OCH(CH₃)₂ 297. SO₂SO₂CH₂CH₃ OCH(CH₃)₂ 298. SO₂ CH₃ OCH(CH₃)₂ 299. SO₂ CF₃ OCH(CH₃)₂ 300.SO₂ OCHF₂ OCH(CH₃)₂ 301. Bond F OCH₂C₆H₅ 302. Bond Cl OCH₂C₆H₅ 303. BondBr OCH₂C₆H₅ 304. Bond NO₂ OCH₂C₆H₅ 305. Bond SCH₃ OCH₂C₆H₅ 306. BondSO₂CH₃ OCH₂C₆H₅ 307. Bond SO₂CH₂CH₃ OCH₂C₆H₅ 308. Bond CH₃ OCH₂C₆H₅ 309.Bond CF₃ OCH₂C₆H₅ 310. Bond OCHF₂ OCH₂C₆H₅ 311. CH₂ F OCH₂C₆H₅ 312. CH₂Cl OCH₂C₆H₅ 313. CH₂ Br OCH₂C₆H₅ 314. CH₂ NO₂ OCH₂C₆H₅ 315. CH₂ SCH₃OCH₂C₆H₅ 316. CH₂ SO₂CH₃ OCH₂C₆H₅ 317. CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ 318. CH₂CH₃ OCH₂C₆H₅ 319. CH₂ CF₃ OCH₂C₆H₅ 320. CH₂ OCHF₂ OCH₂C₆H₅ 321. O FOCH₂C₆H₅ 322. O Cl OCH₂C₆H₅ 323. O Br OCH₂C₆H₅ 324. O NO₂ OCH₂C₆H₅ 325.O SCH₃ OCH₂C₆H₅ 326. O SO₂CH₃ OCH₂C₆H₅ 327. O SO₂CH₂CH₃ OCH₂C₆H₅ 328. OCH₃ OCH₂C₆H₅ 329. O CF₃ OCH₂C₆H₅ 330. O OCHF₂ OCH₂C₆H₅ 331. S F OCH₂C₆H₅332. S Cl OCH₂C₆H₅ 333. S Br OCH₂C₆H₅ 334. S NO₂ OCH₂C₆H₅ 335. S SCH₃OCH₂C₆H₅ 336. S SO₂CH₃ OCH₂C₆H₅ 337. S SO₂CH₂CH₃ OCH₂C₆H₅ 338. S CH₃OCH₂C₆H₅ 339. S CF₃ OCH₂C₆H₅ 340. S OCHF₂ OCH₂C₆H₅ 341. SO₂ F OCH₂C₆H₅342. SO₂ Cl OCH₂C₆H₅ 343. SO₂ Br OCH₂C₆H₅ 344. SO₂ NO₂ OCH₂C₆H₅ 345. SO₂SCH₃ OCH₂C₆H₅ 346. SO₂ SO₂CH₃ OCH₂C₆H₅ 347. SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ 348.SO₂ CH₃ OCH₂C₆H₅ 349. SO₂ CF₃ OCH₂C₆H₅ 350. SO₂ OCHF₂ OCH₂C₆H₅ 351. BondF OSO₂(4-CH₃—C₆H₄) 352. Bond Cl OSO₂(4-CH₃—C₆H₄) 353. Bond BrOSO₂(4-CH₃—C₆H₄) 354. Bond NO₂ OSO₂(4-CH₃—C₆H₄) 355. Bond SCH₃OSO₂(4-CH₃—C₆H₄) 356. Bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) 357. Bond SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) 358. Bond CH₃ OSO₂(4-CH₃—C₆H₄) 359. Bond CF₃OSO₂(4-CH₃—C₆H₄) 360. Bond OCHF₂ OSO₂(4-CH₃—C₆H₄) 361. CH₂ FOSO₂(4-CH₃—C₆H₄) 362. CH₂ Cl OSO₂(4-CH₃—C₆H₄) 363. CH₂ BrOSO₂(4-CH₃—C₆H₄) 364. CH₂ NO₂ OSO₂(4-CH₃—C₆H₄) 365. CH₂ SCH₃OSO₂(4-CH₃—C₆H₄) 366. CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) 367. CH₂ SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) 368. CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) 369. CH₂ CF₃OSO₂(4-CH₃—C₆H₄) 370. CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) 371. O FOSO₂(4-CH₃—C₆H₄) 372. O Cl OSO₂(4-CH₃—C₆H₄) 373. O Br OSO₂(4-CH₃—C₆H₄)374. O NO₂ OSO₂(4-CH₃—C₆H₄) 375. O SCH₃ OSO₂(4-CH₃—C₆H₄) 376. O SO₂CH₃OSO₂(4-CH₃—C₆H₄) 377. O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) 378. O CH₃OSO₂(4-CH₃—C₆H₄) 379. O CF₃ OSO₂(4-CH₃—C₆H₄) 380. O OCHF₂OSO₂(4-CH₃—C₆H₄) 381. S F OSO₂(4-CH₃—C₆H₄) 382. S Cl OSO₂(4-CH₃—C₆H₄)383. S Br OSO₂(4-CH₃—C₆H₄) 384. S NO₂ OSO₂(4-CH₃—C₆H₄) 385. S SCH₃OSO₂(4-CH₃—C₆H₄) 386. S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) 387. S SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) 388. S CH₃ OSO₂(4-CH₃—C₆H₄) 389. S CF₃ OSO₂(4-CH₃—C₆H₄)390. S OCHF₂ OSO₂(4-CH₃—C₆H₄) 391. SO₂ F OSO₂(4-CH₃—C₆H₄) 392. SO₂ ClOSO₂(4-CH₃—C₆H₄) 393. SO₂ Br OSO₂(4-CH₃—C₆H₄) 394. SO₂ NO₂OSO₂(4-CH₃—C₆H₄) 395. SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄) 396. SO₂ SO₂CH₃OSO₂(4-CH₃—C₆H₄) 397. SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) 398. SO₂ CH₃OSO₂(4-CH₃—C₆H₄) 399. SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) 400. SO₂ OCHF₂OSO₂(4-CH₃—C₆H₄) 401. Bond F SCH₃ 402. Bond Cl SCH₃ 403. Bond Br SCH₃404. Bond NO₂ SCH₃ 405. Bond SCH₃ SCH₃ 406. Bond SO₂CH₃ SCH₃ 407. BondSO₂CH₂CH₃ SCH₃ 408. Bond CH₃ SCH₃ 409. Bond CF₃ SCH₃ 410. Bond OCHF₂SCH₃ 411. CH₂ F SCH₃ 412. CH₂ Cl SCH₃ 413. CH₂ Br SCH₃ 414. CH₂ NO₂ SCH₃415. CH₂ SCH₃ SCH₃ 416. CH₂ SO₂CH₃ SCH₃ 417. CH₂ SO₂CH₂CH₃ SCH₃ 418. CH₂CH₃ SCH₃ 419. CH₂ CF₃ SCH₃ 420. CH₂ OCHF₂ SCH₃ 421. O F SCH₃ 422. O ClSCH₃ 423. O Br SCH₃ 424. O NO₂ SCH₃ 425. O SCH₃ SCH₃ 426. O SO₂CH₃ SCH₃427. O SO₂CH₂CH₃ SCH₃ 428. O CH₃ SCH₃ 429. O CF₃ SCH₃ 430. O OCHF₂ SCH₃431. S F SCH₃ 432. S Cl SCH₃ 433. S Br SCH₃ 434. S NO₂ SCH₃ 435. S SCH₃SCH₃ 436. S SO₂CH₃ SCH₃ 437. S SO₂CH₂CH₃ SCH₃ 438. S CH₃ SCH₃ 439. S CF₃SCH₃ 440. S OCHF₂ SCH₃ 441. SO₂ F SCH₃ 442. SO₂ Cl SCH₃ 443. SO₂ Br SCH₃444. SO₂ NO₂ SCH₃ 445. SO₂ SCH₃ SCH₃ 446. SO₂ SO₂CH₃ SCH₃ 447. SO₂SO₂CH₂CH₃ SCH₃ 448. SO₂ CH₃ SCH₃ 449. SO₂ CF₃ SCH₃ 450. SO₂ OCHF₂ SCH₃451. Bond F Cl 452. Bond Cl Cl 453. Bond Br Cl 454. Bond NO₂ Cl 455.Bond SCH₃ Cl 456. Bond SO₂CH₃ Cl 457. Bond SO₂CH₂CH₃ Cl 458. Bond CH₃ Cl459. Bond CF₃ Cl 460. Bond OCHF₂ Cl 461. CH₂ F Cl 462. CH₂ Cl Cl 463.CH₂ Br Cl 464. CH₂ NO₂ Cl 465. CH₂ SCH₃ Cl 466. CH₂ SO₂CH₃ Cl 467. CH₂SO₂CH₂CH₃ Cl 468. CH₂ CH₃ Cl 469. CH₂ CF₃ Cl 470. CH₂ OCHF₂ Cl 471. O FCl 472. O Cl Cl 473. O Br Cl 474. O NO₂ Cl 475. O SCH₃ Cl 476. O SO₂CH₃Cl 477. O SO₂CH₂CH₃ Cl 478. O CH₃ Cl 479. O CF₃ Cl 480. O OCHF₂ Cl 481.S F Cl 482. S Cl Cl 483. S Br Cl 484. S NO₂ Cl 485. S SCH₃ Cl 486. SSO₂CH₃ Cl 487. S SO₂CH₂CH₃ Cl 488. S CH₃ Cl 489. S CF₃ Cl 490. S OCHF₂Cl 491. SO₂ F Cl 492. SO₂ Cl Cl 493. SO₂ Br Cl 494. SO₂ NO₂ Cl 495. SO₂SCH₃ Cl 496. SO₂ SO₂CH₃ Cl 497. SO₂ SO₂CH₂CH₃ Cl 498. SO₂ CH₃ Cl 499.SO₂ CF₃ Cl 500. SO₂ OCHF₂ Cl

Likewise, particular preference is given to the compounds of the formulaIa2 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia2.n, where the variables X, R⁴ and R¹⁰ are as definedin Table 1.

Likewise, particular preference is given to the compounds of the formulaIa3 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia3.n, where the variables X, R⁴ and R¹⁰ are as definedin Table 1.

Likewise, particular preference is given to the compounds of the formulaIa4 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=2), in particularto the compounds Ia4.n, where the variables X, R⁴ and R¹⁰ are as definedin Table 1.

Likewise, particular preference is given to the compounds of the formulaIa5 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia5.n, where the variables X, R⁴ and R¹⁰ are as definedin Table 1.

Likewise, particular preference is given to the compounds of the formulaIa6 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=2), in particularto the compounds Ia6.n, where the variables X, R⁴ and R¹⁰ are as definedin Table 1.

Likewise, particular preference is given to the compounds of the formulaIa7 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia7.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise, particular preference is given to the compounds of the formulaIa8 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia8.n, where the variables X, R⁴ and R¹⁰ are as definedin Table 1.

Likewise, particular preference is given to the compounds of the formulaIa9 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia9.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise, particular preference is given to the compounds of the formulaIa10 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia10.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise, particular preference is given to the compounds of the formulaIa11 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Iall.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise, particular preference is given to the compounds of the formulaIa12 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0) in particular to thecompounds Ia12.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise, particular preference is given to the compounds of the formulaIa13 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia13.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise, particular preference is given to the compounds of the formulaIa14 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia14.n, where the variables X, R⁴ and R¹⁰ are asdefined in Table 1.

Likewise, particular preference is given to the compounds of the formulaIa15 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia15.n, where the variables X, R⁴ and R¹⁰ are asdefined in Table 1.

Likewise, particular preference is given to the compounds of the formulaIa16 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia16.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise particular preference is given to the compounds of the formulaIa17 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia17.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise particular preference is given to the compounds of the formulaIa18 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R¹³=CH₃, m=1), inparticular to the compounds Ia18.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa19 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia19.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise particular preference is given to compounds of the formula Ia20(≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompound Ia20.n, where the variable X, R⁴ and R¹⁰ are as defined intable 1.

Likewise particular preference is given to the compounds of the formulaIa21 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, m=0), in particular to thecompounds Ia21.n, where the variables X, R⁴ and R¹⁰ are as defined inTable 1.

Likewise particular preference is given to the compounds of the formulaIa22 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁶=H, R³=CH₃, m=1), in particularto the compounds Ia22.n, where the variables X, R⁴ and R¹⁰ are asdefined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa23 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=H, m=0), inparticular to the compounds Ia23.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa24 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia24.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa25 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia25.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa26 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=2), in particular to the compounds Ia26.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa27 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia27.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa28 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=2), in particular to the compounds Ia28.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa29 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia29.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa30 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH³,m=1), in particular to the compounds Ia30.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa31 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia31.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa32 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia32.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa33 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia33.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa34 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia34.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa35 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia35.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa36 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia36.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa37 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia37.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa38 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia38.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa39 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia39.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa40 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia40.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa41 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia41.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa42 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia42.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa43 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R¹³=CH₃, m=0), inparticular to the compounds Ia43.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa44 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁴ to R¹⁶=H, R³ and R¹³=CH₃,m=1), in particular to the compounds Ia44.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa45 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵ and R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia45.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa46 (≡Ia where R¹, R², R⁵ and R¹¹, R¹² R¹⁵, R¹⁶=H, R³, R¹³ and R¹⁴=CH₃,m=1), in particular to the compounds Ia46.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa47 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=1), in particular to the compounds Ia47.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa48 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=2), in particular to the compounds Ia48.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa49 (≡Ia where R¹, R², R⁵ and R¹l, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=1), in particular to the compounds Ia49.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa50 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=2), in particular to the compounds Ia50.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa51 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia51.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa52 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH³, m=1), in particular to the compounds Ia52.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa53 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia53.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa54 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia54.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa55 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia55.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa56 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia56.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa57 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia57.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa58 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=1), in particular to the compounds Ia58.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa59 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=1), in particular to the compounds Ia59.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa60 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia60.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa61 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia61.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa62 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R³, R¹³ andR¹⁴=CH₃, m=1), in particular to the compounds Ia62.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa63 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴ CH₃,m=0), in particular to the compounds Ia63.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa64 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia64.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa65 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=H, R¹³ and R¹⁴=CH₃,m=0), in particular to the compounds Ia65.n, where the variables X, R⁴and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa66 (≡Ia where R¹, R², R⁵ and R¹¹, R¹², R¹⁵, R¹⁶=R, R³, R¹³ andR¹⁴=CH₃, m=1), in particular to the compounds Ia66.n, where thevariables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa67 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=1), inparticular to the compounds Ia67.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa68 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia68.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa69 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia69.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa70 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=2), inparticular to the compounds Ia70.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa71 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia71.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa72 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=2), inparticular to the compounds Ia72.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa73 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia73.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa74 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia74.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa75 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia75.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa76 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia76.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa77 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia77.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa78 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia78.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa79 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia79.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa80 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia80.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa81 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia81.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa82 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia82.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa83 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia83.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa84 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia62.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa85 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia85.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa86 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia86.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa87 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹=CH₃, m=0), inparticular to the compounds Ia87.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa88 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R³ and R¹¹=CH₃, m=1), inparticular to the compounds Ia88.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa89 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia89.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa90 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia90.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa91 (≡Ia where R¹, R², R⁵, R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1), inparticular to the compounds Ia91.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa92 (≡Ia where R¹, R², R⁵, R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=2), inparticular to the compounds Ia92.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa93 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia93.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa94 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=2),in particular to the compounds Ia94.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa95 (≡Ia where R¹, R², R⁵ and R¹² to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia95.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa96 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia96.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa97 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia97.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa98 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia98.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa99 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia99.n, where the variables X, R⁴ to R¹⁰ areas defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa100 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia100.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa101 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia101.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa102 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia102.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa103 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia103.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa104 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia104.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa105 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia105.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa106 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia106.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa107 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia107.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa108 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia108.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa109 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R¹¹ and R¹²=CH₃, m=0), inparticular to the compounds Ia109.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa110 (≡Ia where R¹, R², R⁵ and R¹³ to R¹⁶=H, R³, R¹¹ and R¹²=CH₃, m=1),in particular to the compounds Ia110.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa111 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia111.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa112 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia111.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa113 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia113.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa114 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=2),in particular to the compounds Ia114.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa115 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia115.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa116 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=2),in particular to the compounds Ia116.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa117 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia117.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa118 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia118.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa119 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia119.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa120 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia120.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa121 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia121.n, where the variables X, R⁴ to R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa122 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia122.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa123 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia123.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa124 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia124.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa125 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia125.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa126 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia126.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa127 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia127.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa128 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia128.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa129 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia129.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa130 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia130.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa131 (≡Ia where R¹, R², R⁵ and R¹¹ to R¹⁴=H, R¹⁵ and R¹⁶=CH₃, m=0), inparticular to the compounds Ia131.n, where the variables X, R⁴ and R¹⁰are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa132 (≡Ia where R¹, R², R⁵ and R¹l to R¹⁴=H, R³, R¹⁵ and R¹⁶=CH₃, m=1),in particular to the compounds Ia132.n, where the variables X, R⁴ andR¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa133 (≡Ia where R¹, R² and R⁵=H, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ and R¹⁴together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia133.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa134 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia134.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa135 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia135.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa136 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=2), in particular to the compounds Ia136.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa37 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia137.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa138 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=2), in particular to the compounds Ia138.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa139 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia139.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa140 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia140.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa141 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia141.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa142 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia142.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa143 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia143.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa144 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia144.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa145 (=Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹S and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia145.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa146 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia146.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa147 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia147.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa148 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia148.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa149 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia149.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa150 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia150.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa151 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia151.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa152 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia152.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa153 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=0), in particular to the compounds Ia153.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa154 (≡Ia where R¹, R² and R⁵=H, R³, R¹¹, R¹², R¹⁵ and R¹⁶=CH₃, R¹³ andR¹⁴ together with the carbon to which they are attached form a carbonylgroup, m=1), in particular to the compounds Ia154.n, where the variablesX, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa155 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia155.n,where the variables X, R⁴ and R¹⁰ are as defined in Table 1.

Likewise particular preference is given to the compounds of the formulaIa156 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia156.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa157 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia157.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa158 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=2), in particular to the compounds Ia158.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa159 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia159.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa160 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=2), in particular to the compounds Ia160.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa161 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia161.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa162 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia162.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa163 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia163.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa164 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia164.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa165 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia165.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa166 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia166.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa167 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia167.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa168 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia168.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa169 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia169.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa170 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia170.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa171 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia171.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa172 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia172.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa173 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia173.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa174 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia174.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa175 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=0), in particular to the compounds Ia175.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

Likewise particular preference is given to the compounds of the formulaIa176 (≡Ia where R¹, R², R⁵ and R¹¹, R¹³ to R¹⁵=H, R¹² and R¹⁶ togetherform a —(CH₂)₂— chain, m=1), in particular to the compounds Ia176.n,where the variables X, R⁴ and R¹⁰ are as defined in Table I [sic].

The tricyclic benzoylcyclohexanedione derivatives of the formula I canbe obtained by various routes, for example by one of the followingprocesses:

A. Preparation of compounds of the formula I where R¹⁰=halogen byreacting a tricyclic benzoylcyclohexanedione derivative of the formulaIα (≡I where R¹⁰=hydroxyl) with a halogenating agent:

Suitable halogenating agents are, for example, phosgene, diphosgene,triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride,phosphorus pentachloride, mesyl chloride,chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide,phosphorus oxybromide, etc.

The starting materials are generally employed [lacuna] equimolaramounts. However, it may also be advantageous to employ an excess of oneor the other component.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene or chlorobenzene, polar aprotic solvents, suchas acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures ofthese. However, it is also possible to carry out the reaction in theabsence of solvent.

The reaction temperature is generally in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to afford theproduct.

B. Preparation of compounds of the formula I where R¹⁰=OR¹⁷ or OSO₂R¹⁸,by reacting a tricyclic benzoylcyclohexanedione derivative of theformula Iα (≡I where R¹⁰=hydroxyl) with an alkylating agent IIIα or asulfonylating agent IIIβ.

L¹ is a nucleophilically replaceable leaving group, such as halogen, forexample chlorine or bromine, hetaryl, for example imidazolyl,carboxylate, for example acetate, or sulfonate, for example mesylate ortriflate, etc.

The compounds of the formula IIIα or IIIβ can be employed directly, suchas, for example, in the case of the carbonyl halides, or be generated insitu, for example activated carboxylic acids (using carboxylic acid anddicyclohexylcarbodiimide etc.).

The starting materials are generally employed in equimolar amounts.However, it may also be advantageous to employ an excess of one or theother component.

If appropriate, it may also be advantageous to carry out the reaction inthe presence of a base. Here, the reactants and the base areadvantageously employed in equimolar amounts. In certain cases, anexcess of base, for example from 1.5 to 3 molar equivalents, may beadvantageous.

Suitable bases are tertiary alkylamines, such as triethylamine, aromaticamines, such as pyridine, alkali metal carbonates, for example sodiumcarbonate or potassium carbonate, alkali metal bicarbonates, such assodium bicarbonate and potassium bicarbonate, alkali metal alkoxides,such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, oralkali metal hydrides, for example sodium hydride. Preference is givento using triethylamine or pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene or chlorobenzene, ethers, such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aproticsolvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide,or esters, such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to afford theproduct.

C. Preparation of compounds of the formula I where R¹⁰=OR¹⁷, SR¹⁷,OSO₂R¹⁸, NR¹⁹R²⁰ or N-bonded heterocyclyl by reacting compounds of theformula Iβ (≡I where R¹⁰=halogen) with a compound of the formula IVα,IVβ, IVγ, IVδ or IVε, if appropriate in the presence of a base or withprior formation of salt.

HOR¹⁷ IVα or Iβ + HSR¹⁷ IVβ → I(where R¹⁰ = or OR¹⁷, SR¹⁷, OSO₂R¹⁸,NR¹⁹R²⁰ or N-bonded heterocyclyl) HOSO₂R¹⁸ IVγ or HNR¹⁹R²⁰ IVδ orH(N-bonded IVε heterocyclyl)

The starting materials are generally employed in equimolar amounts.However, it may also be advantageous to employ an excess of one or theother component.

If appropriate, it may also be advantageous to carry out the reaction inthe presence of a base. Here, the reactants and the base areadvantageously employed in equimolar amounts. An excess of base, forexample can [sic] 1.5 to 3 molar equivalents, based on Iβ (whereR¹⁰=halogen), may be advantageous in certain cases.

Suitable bases are tertiary alkylamines, such as triethylamine, aromaticamines, such as pyridine, alkali metal carbonates, for example sodiumcarbonate or potassium carbonate, alkali metal bicarbonates, such assodium bicarbonate and potassium bicarbonate, alkali metal alkoxides,such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, oralkali metal hydrides, for example sodium hydride. Preference is givento using sodium hydride or potassium tert-butoxide.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene or chlorobenzene, ethers, such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aproticsolvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide,or mixtures of these.

The reaction temperature is generally in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to afford theproduct.

D. Preparation of compounds of the formula I where R¹⁰=SOR¹⁸, SO₂R¹⁸, byreacting compounds of the formula I where R¹⁰=SR¹⁸ (Iγ) with anoxidizing agent.

Suitable oxidizing agents are, for example, m-chloroperbenzoic acid,peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, ifappropriate in the presence of a catalyst, such as tungstate.

The starting materials are generally employed in equimolar amounts.However, it may also be advantageous to employ an excess of one or theother component.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, forexample, toluene, xylene or chlorobenzene, ethers, such as diethylether, methyltert-butyl ether, tetrahydrofuran or dioxane, polar aproticsolvents, such as acetonitrile or dimethylformamide, or esters, such asethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to afford theproduct.

E. Preparation of compounds of the formula Iα (≡I where R¹⁰=hydroxyl) byreacting an activated tricyclic benzoic acid of the formula VIα or atricyclic benzoic acid VIβ, preferably activated in situ, with acyclohexanedione of the formula V to give the acylation product VII,followed by rearrangement.

L² is a nucleophilically replaceable leaving group, such as halogen, forexample bromine or chlorine, hetaryl, for example imidazolyl or pyridyl,carboxylate, for example acetate or trifluoroacetate, etc.

The activated tricyclic benzoic acid VIa can be employed directly, suchas in the case of the tricyclic benzoyl halides, or be generated insitu, for example using dicyclohexylcarbodiimide,triphenylphosphine/azodicarboxylic ester, 2-pyridinedisulfide/triphenylphosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylationreaction in the presence of a base. Here, the reactants and theauxiliary base are advantageously employed in equimolar amounts. Aslight excess of auxiliary base, for example from 1.2 to 1.5 molarequivalents, based on VI, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine, or alkalimetal carbonates. Suitable solvents are, for example, chlorinatedhydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatichydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane,polar aprotic solvents, such as acetonitrile, dimethylformamide ordimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures ofthese.

If tricyclic benzoyl halides are employed as activated carboxylic acidcomponents, it may be advantageous to cool the reaction mixture to 0-10°C. when adding this reaction partner. The mixture is subsequentlystirred at 20-100° C., preferably at 25-50° C., until the reaction hasgone to completion. Work-up is carried out in a customary manner, forexample by pouring the reaction mixture into water and extracting theproduct of value. Solvents which are suitable for this purpose are, inparticular, methylene chloride, diethyl ether and ethyl acetate. Theorganic phase is dried and the solvent removed, and the crude ester canthen be employed for the rearrangement without further purification.

The rearrangement of the esters VII to give the compounds of the formulaIα is advantageously carried out at from 20 to 100° C. in a solvent andin the presence of a base and, if appropriate, using a cyano compound ascatalyst.

Solvents which may be used are, for example, acetonitrile, methylenechloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene ormixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromaticamines, such as pyridine, or alkali metal carbonates, such as sodiumcarbonate or potassium carbonate, which are preferably employed inequimolar amounts or in an up to fourfold excess, based on the ester.Preference is given to using triethylamine or alkali metal carbonate,preferably in double the equimolar ratio, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanideor potassium cyanide, and organic cyano compounds, such as acetonecyanohydrin or trimethylsilyl cyanide. They are employed in an amount offrom 1 to 50 mol percent, based on the ester. Preference is given tousing acetone cyanohydrin or trimethylsilyl cyanide, for example in anamount of from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up may be carried out in a manner known per se. The reactionmixture is, for example, acidified using dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride or ethyl acetate. Theorganic extract can be extracted with 5-10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified and the resulting precipitateis filtered off with suction and/or extracted with methylene chloride orethyl acetate, the extract being dried and concentrated.

The tricyclic benzoyl halides of the formula VIα where L²=Cl, Br can beprepared in a manner known per se by reacting the tricyclic benzoicacids of the formula VIβ (≡VIb) with halogenating reagents such asthionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene,oxalyl chloride and oxalyl bromide.

In a known manner, the tricyclic benzoic acids of the formula VIβ (≡VIb)can be prepared by acidic or basic hydrolysis from the correspondingesters VIc.

Tricyclic benzoic acid derivatives of the formula VI

where:

X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;

Y together with the two carbons to which it is attached forms asaturated, partially saturated or unsaturated 5- or 6-memberedheterocycle which contains one to three identical or differentheteroatoms selected from the following group: oxygen, sulfur ornitrogen;

R¹,R²,R⁶,R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)-aminosulfonyl,N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino,N—(C₁--C₆-haloalkylsulfonyl)amino,N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino orN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;

R⁵ is hydrogen, C₁-C₆-alkyl or halogen;

R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl,formyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl;

m is 0, 1 or 2;

R²¹ is hydroxyl or a radical which can be removed by hydrolysis;

are novel and also form part of the subject matter of the invention.

Examples of radicals which can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals which can be unsubstituted orsubstituted, halides, heteroaryl radicals which are attached vianitrogen, amino and imino radicals which may be unsubstituted orsubstituted, etc.

Preference is given to tricyclic benzoyl halides VIa (VI whereR²¹=halogen)

where

the variables X, Y, R¹ to R⁵ and m are as defined under formula VI and

Hal is halogen, in particular chloride or bromide.

Preference is also given to tricyclic benzoic acids of the formula VIb(VI where R¹⁷ [sic]=hydroxyl; VIγ),

where the variables X, Y, R¹ to R⁵ and m are as defined under formulaVI.

Preference is also given to tricyclic benzoic esters of the formula VIc(VI where R²¹=T=C₁-C₆-alkoxy),

where

the variables X, Y, R¹ to R⁵ and m are as defined under formula VI and

T is C₁-C₆-alkoxy.

With respect to the variables X, Y, R¹ to R⁵ and m, the particularlypreferred embodiments of the tricyclic benzoic acid derivatives of theformulae VI, VIa, VIb and VIc correspond to those of the tricyclicbenzoylcyclohexanedione derivatives of the formula I.

Particular preference is given to the compounds VI, VIa, VIb and VIcwhere Y together with the two carbons to which it is attached forms thefollowing heterocycles:

Here, extraordinary preference is given to the compounds VI, VIa, VIband VIc where

R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in particularC₁-C₆-alkylsulfonyl.

The tricyclic benzoic esters VIc can be obtained in different ways.

For example, benzoic esters of the formula VIII, which are prepared in amanner known per se (cf., for example, Chem. Pharm. Bull. 1985, 33 (8),3336; Helv. Chim. Acta 1987, 70, 1326; J. Chem. Soc. Perkin Trans. 1972,2019; J. Chem. Soc. Perkin Trans. 1991, 2763; Tetrahydron Asymmetry1998, 9, 1137), can be cyclized to cyclic ketones of the formula IX(cf., for example, Chem. Ber. 1923, 56, 1819; J. Chem. Soc. Perkin I1991, 2763; J. Med. Chem. 1988, 31, 230; Tetrahedron 1987, 43, 4549;Synlett 1991, 6, 443; Chem. Pharm. Bull. 1985, 33 (8), 3336).Analogously to known processes (cf., for example, J. Heterocyclic Chem.1976, 13, 545; J. Heterocyclic Chem. 1972, 9, 1341; J. Org. Chem. 1978,43, 3015; J. Chem. Soc. Perkin Trans. I 1978, 86; J. Org. Chem. 1986,51, 2021), these can be converted into the tricyclic benzoic esters ofthe formula VIc.

Furthermore, it may be suitable to acetylate the cyclic ketone of theformula IX in a manner known per se (X), for example using an anhydrideor acid anhydride, if appropriate in the presence of catalytic amountsof a Lewis acid, such as boron trifluoride (cf., for example, Can. J.Chem. 1979, 57, 3292; J. Am. Chem. Soc. 1953, 75, 626), followed byreaction with a hydrazine (cf. A. R. Katritzky et al., ComprehensiveHeterocyclic Chemistry, Vol. 5, p. 121, 277-280 (1984), Pergamon Press;J. Org. Chem. 1961, 26, 451; Org. Synth. 1949, 29, 54), where theresulting pyrazole radical can be modified further by customaryprocesses.

Furthermore, the diketone X can be reacted with hydroxylamine orequivalents thereof (cf. A. R. Katritzky et al., ComprehensiveHeterocyclic Chemistry, Vol. 6, p. 61-64, 118 (1984), Pergamon Press;Chem. Ber. 1967, 100, 3326). This gives corresponding isoxazolederivatives which can be modified further by customary processes.

It is also possible to react the diketone X with amidines (cf., forexample, A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry,Vol. 3, p. 112-114 (1924), Pergamon Press; J. Chem. Soc. C 1967, 1922;Org. Synth. 1963, IV, 182). If required, the resulting pyrimidinederivatives can be modified further by customary processes.

In the reactions mentioned above, it is also possible to employ, insteadof the diketone X, equivalents thereof, such as enol ethers or enamines,which can be prepared analogously to known processes.

It may also be possible to react the cyclic ketone of the formula IXanalogously to known processes with an aldehyde or ketone (XI) (cf., forexample, Tetrahedron Lett. 1978, 2111; Tetrahedron Lett. 1981, 5251;Chem. Ber. 1960, 2294; J. Chem. Soc. Perkin Trans. 1, 1991, 1467;Tetrahedron Lett. 1992, 8091). The resulting unsaturated cyclic ketoneof the formula XI can be reacted with a hydrazine in a manner known perse (cf., for example, A. R. Katritzky et al. Comprehensive HeterocyclicChemistry, Vol. 2, 6 (1984), Pergamon Press; J. Heterocyclic Chem. 1969,533; J. Heterocyclic Chem. 1968, 853), where the resulting pyrazolinecan be modified further by customary processes.

It is furthermore possible to react the unsaturated cyclic ketone of theformula XI with hydroxylamine or equivalents thereof (Z. Chem. 1980, 20,19). This gives corresponding isoxazoline derivatives, which can bemodified further by customary processes.

Furthermore, it is possible to convert aldehydes of the formula XII,which can be prepared in a manner known per se, analogously to processesknown from the literature by reaction with a hydrazine or hydroxylamine(or equivalents of these) into corresponding hydrazones or oximes (cf.,for example, Synth. Commun. 1990, 20, 1373; J. Org. Chem. 1980, 45,3756). These in turn can be converted in a manner known per se into thecorresponding 1,3-dipoles, which then react in a [3+2]-cyclo addition togive the compounds VIc (cf., for example, Synth. Commun. 1990, 20, 1373;EP-A 386 892; J. Org. Chem. 1980, 45, 3756; Tetrahedron Lett. 1981, 22,1333.)

The resulting pyrazoles or pyrazolines and isoxazoles or isoxazolinescan be modified further by customary processes.

It is also possible to react the cyclic ketone of the formula IX with adithiol or a “mixed alcohol” analogously to processes known from theliterature (cf., for example, T. W. Greene et al., Protective Groups inOrganic Synthesis, John Wiley & Sons, 133-140), and to subject itsubsequently to a rearrangement in the presence of bromine or a suitableLewis acid, such as, for example, tellurium tetrachloride (cf.Tetrahedron 1991, 47, 4187; Synthesis 1991, 223; J. Chem. Am. [sic] Soc.Chem. Commun. 1985, 1645).

The resulting heterocycles can, if desired, be modified further byprocesses known per se.

The abovementioned substituents R^(3a) are hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;furthermore, the abovementioned radicals R^(3b) are hydrogen,C₁-C₆-alkyl or C₁-C₆-haloalkyl.

The tricyclic benzoic esters of the formula VIc or the tricyclic benzoicacids of the formula VIb can be obtained by reacting a tricyclic benzenederivative of the formula XIII with a C₁-C₆-alcohol or water in thepresence of carbon monoxide, a catalyst and a base.

L³ is a leaving group, such as halogen, for example chlorine, bromine oriodine, or sulfate, such as mesylate or triflate; preference is given tobromine or triflate.

Suitable catalysts are palladium ligand complexes in which the palladiumis present in oxidation state 0, metallic palladium, if appropriateapplied to a support, and preferably palladium(II) salts. The reactionwith palladium(II) salts and metallic palladium is preferably carriedout in the presence of complex ligands.

A suitable palladium(0) ligand complex is, for example,tetrakis(triphenylphosphane)palladium.

Metallic palladium is preferably applied to an inert carrier, such as,for example, activated carbon, silica, alumina, barium sulfate orcalcium carbonate. The reaction is preferably carried out in thepresence of complex ligands, such as, for example, triphenylphosphane.

Suitable palladium(II) salts are, for example, palladium acetate andpalladium chloride. Preference is given to carrying out the reaction inthe presence of complex ligands such as, for example,triphenylphosphane.

Suitable complex ligands for the palladium ligand complexes, or complexligands in whose presence the reaction with metallic palladium orpalladium(II) salts is preferably carried out are tertiary phosphaneswhose structure is represented by the following formulae:

where n is a number from 1 to 4 and the radicals R^(a) to R^(g) areC₁-C₆-alkyl, aryl-C₁-C₂-alkyl or preferably aryl. Aryl is, for example,naphthyl and unsubstituted or substituted phenyl such as, for example,2-tolyl and in particular unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per sestarting from commercially available palladium salts, such as palladiumchloride or palladium acetate, and the corresponding phosphanes, suchas, for example, triphenylphosphane or 1,2-bis(diphenylphosphano)ethane.A large number of complexed palladium salts is also commerciallyavailable. Preferred palladium salts are[(R)-(+)-2,2′-bis(diphenylphosphano)-1,1′-binaphthyl]palladium(II)chloride, bis(triphenylphosphane)palladium(II) acetate and in particularbis(triphenylphosphane)palladium(II) chloride.

The palladium catalyst is generally employed in a concentration of from0.05 to 5 mol %, and preferably of 1-3 mol %.

Suitable bases are tertiary amines, such as, for example,N-methylpiperidine, ethyldiisopropylamine,1,8-bisdimethylaminonaphthalene and in particular triethylamine. Alsosuitable are alkali metal carbonates, such as sodium carbonate orpotassium carbonate. However, mixtures of potassium carbonate andtriethylamine are also suitable.

In general, from 2 to 4 molar equivalents, in particular 2 molarequivalents, of the alkali metal carbonate, and from 1 to 4 molarequivalents, in particular 2 molar equivalents, of the tertiary amineare employed, based on the tricyclic benzene derivative of the formulaIX.

Suitable solvents are nitrites, such as benzonitrile and acetonitrile,amides, such as dimethylformamide, dimethylacetamide,tetra-C₁-C₄-alkylureas or N-methylpyrrolidone, and preferably ethers,such as tetrahydrofuran, methyl tert-butyl ether. Particular preferenceis given to using, as solvents, ethers such as 1,4-dioxane anddimethoxyethane

Furthermore, the tricyclic benzoic acids of the formula VIb can beobtained by converting a tricyclic benzene derivative of the formulaXIII where L³ is halogen, such as chlorine or bromine, in particularbromine, by reaction with, for example, n-butyllithium or magnesium intothe metalated derivative, followed by quenching with carbon dioxide(cf., for example, J. Org. Chem. 1990, 55, 773; Angew. Chem. Int. Ed.1969, 8, 68).

It is also possible to obtain the tricyclic benzoic acids VIb byhydrolyzing the corresponding nitriles, analogously to processes knownfrom the literature. The nitriles for their part can be obtained byhalogen/nitrile exchange or by Sandmeyer reaction from the correspondinganilines XIV.

The compounds of the formula XIII,

where:

X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;

Y together with the two carbons to which it is attached forms asaturated, partially saturated or unsaturated 5- or 6-memberedheterocycle which contains one to three identical or differentheteroatoms selected from the following group: oxygen, sulfur ornitrogen;

R¹,R²,R⁶,R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl,N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino,N—(C₁-C₆-haloalkylsulfonyl)amino,N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino orN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;

R⁵ is hydrogen, C₁-C₆-alkyl or halogen;

R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl,formyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl;

m is 0, 1 or 2;

L³ is halogen, C₁-C₆-alkylsulfonyloxy, C₁-C₆-haloalkylsulfonyloxy orphenylsulfonyloxy, where the phenyl ring of the last-mentioned radicalmay be unsubstituted or partially or fully halogenated and/or may carryone to three of the following radicals: nitro, cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

are novel and also form part of the subject matter of the invention.

Preference is given to compounds of the formula XIII where L³ ishalogen, in particular bromine.

The particularly preferred embodiments of the compounds of the formulaXIII with respect to the variables X, Y, R¹ to R⁵ and m correspond tothose of the tricyclic benzoylcyclohexanedione derivatives of theformula I.

Particular preference is given to the compounds of the formula XIIIwhere

Y together with the two carbons to which it is attached forms thefollowing heterocycles:

Here, extraordinary preference is given to the compounds XIII where

R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in particularC₁-C₆-alkylsulfonyl.

The compounds of the formula XIII can be obtained in different ways, thefused system, for example, can be constructed analogously to theprocesses described for the compounds of the formula VIc.

However, it is also possible to construct the fused system from asuitable parent compound (analogously to the processes described forcompounds of the formula VIc) and to introduce L³=halogen subsequentlyby customary halogenating reactions.

The anilines of the formula XIV and the nitriles of the formula XV

where:

X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;

Y together with the two carbons to which it is attached forms asaturated, partially saturated or unsaturated 5- or 6-memberedheterocycle which contains one to three identical or differentheteroatoms selected from the following group: oxygen, sulfur ornitrogen;

R¹,R²,R⁶,R⁷ are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R³ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy;

R⁴ is nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)aminosulfonyl,N,N-di(C₁-C₆-alkyl)aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)amino,N—(C₁-C₆-haloalkylsulfonyl)amino,N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)amino orN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)amino;

R⁵ is hydrogen, C₁-C₆-alkyl or halogen;

R8 is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl,formyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl;

m is 0, 1 or 2;

are also novel and form part of the subject matter of the invention.

The particularly preferred embodiments of the compounds of the formulaeXIV and XV with respect to the variables X, Y, R¹ to R⁵ and m correspondto those of the tricyclic benzoylcyclohexanedione derivatives of theformula I.

Particular preference is given to the compounds of the formula XV [sic]or XVI [sic] where

Y together with the two carbons to which it is attached forms thefollowing heterocycles:

Here, extraordinary preference is given to the compounds XIV or XV where

R⁴ is nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; in particularC₁-C₆-alkylsulfonyl.

The compounds of the formula XIV can be obtained in different ways; forexample, the fused system can be constructed analogously to theprocesses described for the compounds of the formula VIc.

However, it is also possible to construct the fused system from asuitable parent compound (analogously to the processes described for thecompounds of the formula VIc) and to introduce a nitro groupsubsequently by nitration para to R⁴, analogously to processes knownfrom the literature, and to convert this group in a manner known per seby reduction into the amino group.

If appropriate, it may be advantageous in the synthesis variantsdescribed above to introduce protective groups for certainfunctionalities if the functionalities are not compatible with thereaction conditions required.

The selection of the protective groups depends both on the reactionconditions and on the structure of the molecule. The protective groups,their introduction and their removal are generally known from theliterature (cf., for example, T. W. Greene et al., “Protective Groups inOrganic Synthesis”, 2^(nd) edition, Wiley, New York, 1991), and they canbe employed analogously to processes known from the literature.

Furthermore, it may be necessary to carry out a combination of thesynthesis variants described above.

It is also possible to introduce further substituents or to modify thesubstituents present by electrophilic, nucleophilic, free-radical ororganometallic reactions and by oxidation or reduction reactions

PREPARATION EXAMPLES 1.(5,5-Dimethyl-1,3-dioxocyclohex-2-yl)(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone(Compound 2.2) Methyl 2-hydroxy-3-formyl-4-methoxy-benzoate

At from 0 to 5° C., a solution of 209.0 g (1.1 mol) of titaniumtetrachloride in 150 ml of methylene chloride was added dropwise to asolution of 50.1 g (0.275 mol) of methyl 2-hydroxy-4-methoxybenzoate and88 g (0.725 mol) of dichloromethoxymethane in 400 ml of methylenechloride, and the mixture was stirred at room temperature overnight. Themixture was subsequently added to ice-water with stirring and extractedwith methylene chloride. The combined organic phases were washed withsodium bicarbonate solution, water and sodium chloride solution anddried, and the solvent was then removed. Chromatography over silica gelusing cyclohexane/ethyl acetate=1:1 gave 24.5 g (42%) of methyl2-hydroxy-3-formyl-4-methoxy benzoate in the form of a colorless solidof m.p.: 123-124° C.

¹H-NMR (CDCl₃, δ in ppm): 3.92 (s, 3H); 3.98 (s, 3H); 6.49 (d, 1H); 8.19(d, 1H); 10.39 (s, 1H).

Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

At room temperature, 23.2 g (0.192 mol) of allyl bromide were addeddropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500ml of dimethyl sulfoxide, and the mixture was stirred at roomtemperature for 4 hours. The mixture was subsequently added to 1.5 l of3% strength aqueous hydrochloric acid with stirring and extracted withethyl acetate. The combined organic phases were washed with water anddried, and the solvent was removed. Chromatography over silica gel usingcyclohexane/ethyl acetate=1:2 gave 7.7 g (36% of methyl2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

¹H-NMR (CDCl₃, δ in ppm): 3.86 (s, 3H); 3.93 (s, 3H); 4.58 (d, 2H); 5.32(d, 1H); 5.39 (d, 1H); 6.15 (m, 1H); 6.79 (d, 1H); 8.04 (d, 1H); 10.41(s, 1H).

6-Methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin

Step a)

At room temperature, 4.6 g (18.4 mol) of methyl2-allyloxy-3-formyl-4-methoxybenzoate in 70 ml of methanol were addeddropwise to a solution of 2.25 g (32.3 mmol) of hydroxylammoniumchloride and 2.7 g of pyridine in 70 ml of water. The mixture wasstirred at room temperature overnight, 150 ml of water were added, themixture was extracted with methylene chloride, the combined organicphases were washed with 3% strength aqueous hydrochloric acid and driedand the solvent was removed. The resulting oxime had a melting point of126-129° C.

Step b)

This oxime was reacted further without further purification bydissolving it in 40 ml of methylene chloride and adding 15.0 ml (25.0mmol) of sodium hydrochloride [sic] solution (12.5% of active chlorine)dropwise. A spatula tip of sodium acetate was added and the mixture wasstirred at room temperature for 12 hours. The organic phase wasseparated off, the aqueous phase was extracted with methylene chloride,the combined organic phases were washed with water and dried and thesolvent was removed. Chromatography over silica gel usingcyclohexane/ethyl acetate=1:1 gave 2.2 g (49%) of6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolinein the form of a colorless solid of m.p.: 199-203° C.

¹H-NMR (CDCl₃, δ in ppm): 3.84 (s, 3H); 3.98 (s, 3H); 3.8-4.0 (m, 2H);4.16 (dt, 1H); 4.63 (t, 1H); 4.84 (dd, 1H); 6.61 (d, 1H); 7.93 (d, 1).

6-Methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline

At room temperature, a solution of 0.8 g (20.0 mmol) of sodium hydroxidein 7 ml of water was added dropwise to a solution of 2.1 g (8.0 mmol) of6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolinein 40 ml of methanol, and the mixture was heated under reflux for 6hours. After cooling, the solvent was removed and the residue was takenup in about 50 ml of water and washed with methylene chloride. Theaqueous phase was subsequently acidified using 10% strength hydrochloricacid (pH=1-2), and the precipitate was filtered off with suction, washedwith water and dried at 60° C. This gave 1.7 g (86%) of6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolinein the form of colorless crystals.

¹H-NMR (CDCl₃, δ in ppm): 3.73 (dd, 1H); 3.89 (s, 3H); 3.84-3.95 (m,1H); 4.11 (dd, 1H); 4.54 (dd, 1B); 4.79 (dd, 1H); 6.61 (d, 1H); 7.81 (d,1H).

(5,5-Dimethyl-1,3-dioxocyclohex-2-yl)(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone(Compound 2.2)

Step a)

At room temperature, 0.26 g (2.2 mol) of thione [sic] chloride and adrop of dimethyl formamide were added to a solution of 0.50 g (2.0 mmol)of6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolinein 30 ml of carbon tetrachloride, and the mixture was stirred at 40-50°C. for 3 hours. The solvent was subsequently removed under reducedpressure. This gave, in quantitative yield (0.54 g),6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline as abrownish oil.

0.54 g (2.0 mmol) of6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline wasdissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to asolution of 0.28 g (2.0 mmol) of 5,5-dimethylcyclohexan-1,3-dione and0.6 g (6.0 mmol) of triethylamine in 20 ml of acetonitrile. After 12hours of stirring at room temperature, the solvent was removed and theresidue was taken up in methylene chloride and washed with water. Themixture was dried and the solvent was distilled off. The residue wastaken up in 25 ml of acetonitrile and decomposed [sic] with 0.59 g (6.0mmol) of trimethylsilyl cyanide, and the mixture was stirred at 40° C.for 5 hours. After filtration, the solvent was removed and the residuewas chromatographed using cyclohexane/ethyl acetate. This gave 0.59 g(79%) of the compound 2.2 as colorless crystals of melting point203-206° C.

¹H-NMR (CDCl₃, g [sic] in ppm): 1.09 (s, 6H); 2.31 (s, 1H); 2.62 (s,1H); 3.7-4.1 (m, 6H); 4.52 (dd, 1H); 4.61 (dd, 1H); 6.62 (d, 1H); 7.43(d, 1H); 17.0 (Cs, 1H).

2. (5-Bromo-8-methylsulfonyl-3a,4-diyhdro-3H-indeno[1,2-c]isoxazol2-Allyl-6-chlorobenzaldehyde

Under an atmosphere of protective gas, a solution of 10.89 g (0.107 mol)of trimethylethylenediamine in 50 ml of anhydrous tetrahydrofuran wascooled to −10° C. and mixed dropwise with 66.6 ml of a 1.6 molarn-butyllithium solution in hexane (0.107 mol). After 10 minutes, 15 g(0.107 mol) of 6-chlorobenzaldehyde in 70 ml of tetrahydrofuran wereadded dropwise, and the mixture was admixed with a further 0.214 mol ofn-butyllithium in hexane (146.8 ml) and stirred at 0° C. for 2.5 hours.The mixture was cooled to −20° C., 12.42 g (0.139 mol) of copper(I)cyanide were added, the mixture was stirred at −10° C. for 30 minutesand 28.42 g of allyl bromide in 100 ml of tetrahydrofuran were thenadded dropwise. Stirring was continued at 0° C. for 2.5 hours, and 230ml of saturated ammonium chloride solution were then added dropwise. Theresulting solid was separated off and the aqueous phase was extractedwith diethyl ether. The combined organic phases were then washed withsaturated ammonium chloride solution and dried, and the solvent wasremoved under reduced pressure. This gave 17.0 g of2-alkyl-6-chlorobenzaldehyde [sic] (89%) in the form of a dark oil.

¹H-NMR (CDCl₃, δ in ppm): 3.73 (d, 2H); 5.05 (dd, 2H); 5.96 (m, 1H);7.05-7.48 (m, 3H); 10.58 (s, 1H).

2-Allyl-6-chlorobenzaldehyde oxime

5.58 g of sodium bicarbonate were added to a solution of 4.62 g ofhydroxylamine hydrochloride in 50 ml of water, and the mixture wascooled to 0° C. A solution of 9.7 g (44.32 mmol) of2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was added, and themixture was stirred at room temperature overnight. The methanol wassubsequently removed under reduced pressure and the residue was addedwith stirring to 300 ml of water. The aqueous phase was extracted withdiethyl ether, the combined organic phases were washed with saturatedammonium chloride solution and dried and the solvent was removed. Thisgave 8.7 g (quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in theform of a viscous oil.

¹H-NMR (CDCl₃, δ in ppm): 3.58 (d, 2H); 5.02 (2d, 2H); 5.95 (m, 1H);7.08-7.36 (m, 3H); 8.49 (s, 1H).

8-Chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazol

At room temperature, 37.0 ml of a sodium hypochloride [sic] solution(12.5% of active chlorine) were added dropwise to a solution of 8.4 g(42.9 mmol) of 2-allyl-6-chlorobenzaldehyde oxime in 100 ml of methylenechloride, and a spatula tip of sodium acetate was added. The mixture wasstirred at room temperature for 2 hours, the organic phase was separatedoff, the aqueous phase was extracted with methylene chloride and thecombined organic phases were washed with saturated ammonium chloridesolution and dried, and the solvent was removed. This gave 7.0 g (94%)of 8-chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazol in the form of aviscous oil.

¹H-NMR (CDCl₃, δ in ppm): 2.81 (dd, 1H); 3.24 (dd, 1H); 3.78-4.03 (s,2H); 4.78 (t, 1H); 7.23-7.41 (m, 3H).

8-Methylthio-3a,4-dihydro-3H-indeno[1,2c]isoxazol

At room temperature, 3.6 g (52.0 mmol) of sodium thiomethoxide wereadded to a solution of 5.0 g (25.8 mmol) of8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazol in 60 ml ofN-methylpyrrolidone, and the mixture was stirred overnight. The mixturewas subsequently added with stirring to 800 ml of water, the aqueousphase was extracted with diethyl ether, the combined organic phases werewashed with saturated ammonium chloride solution and dried and thesolvent was removed. This gave 4.6 g (87%) of8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazol in the form of adark-brown solid.

¹H-NMR (CDCl₃, δ in ppm): 2.54 (s, 3H); 2.78 (dd, 1H); 3.21 (dd, 1H);3.72-3.93 (s, 2H); 4.64 (t, 1H); 7.09-7.38 (m, 3H).

5-Bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazol

120 ml of sulfuric acid (98 percent strength) were cooled to 0° C., and11.2 g (54.8 mmol) of 8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazolwere added a little at a time. 9.2 g (57.5 mmol) of bromine were thenadded dropwise, and the mixture was stirred at 0° C. for 2 hours. Theresulting solution was poured into 2 l of a mixture of water and ice,the mixture was stirred for 1.5 hours and the precipitated solid wasfiltered off with suction and then washed and dried. This gave 11.4 g(73%) of 5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazol of abrown solid of m.p. 127-135° C.

¹H-NMR (CDCl₃, δ in ppm): 2.53 (s, 3H); 2.71 (dd, 1H); 3.24 (dd, 1H);3.81-4.02 (s, 2H); 4.71 (t, 1H); 7.01 (d, 1H); 7.47 (d, 1H).

5-Bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol

A solution of 11.2 g (39.4 mmol) of5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazol and 1.55 g ofsodium tungstate in 250 ml of toluene and 50 ml of glacial acetic acidwas heated to 70° C. and admixed dropwise with 10.73 g (39 percentstrength, 86.8 mmol) of hydrogen peroxide. Stirring at 70° C. wascontinued for 3 hours, and a solid precipitated out. The mixture wasallowed to cool to room temperature and stirred into 1 l of water, andthe white solid was filtered off with suction. The organic phase of thefiltrate was separated off and the aqueous phase was extracted withethyl acetate. The combined organic phases were washed with water anddried and the solvent was removed. This gave a viscous brown oil whichwas stirred with hexane/ethyl acetate (4:1). The resulting precipitatewas filtered off with suction and combined with the solid which had beenobtained above. This gave 7.3 g (59%) of5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol.

¹H-NMR (d⁶-DMSO, δ in ppm): 2.93 (dd, 1H); 3.23 (dd, 1H); 3.41 (s, 3H);3.94 (dd, 1H); 4.16 (m, 1H); 4.81 (t, 1H); 7.82 (d, 1H); 8.03 (d, 1H).

3. 2-Methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazolMethyl 2-chlorosulfonyl-4-chlorobenzoate

At from 0 to 5° C., a solution of 60.9 g (0.88 mol) of sodium nitrite in100 ml of water was added dropwise to a solution of 139 g (0.75 mol) ofmethyl 2-amino-4-chlorobenzoate in 400 ml of concentrated hydrochloricacid, and stirring at 0° C. was continued for 1 hour.

In a second apparatus, 3 g of copper(II) chloride, 3 g ofbenzyltriethylammonium chloride, 10 ml of water and 400 ml of1,2-dichloroethane were combined and 64 g (1 mol) of sulfur dioxide wereintroduced.

The diazonium salt was then added at 10 to 15° C. as described above[sic], and the mixture was slowly heated to 50° C. A further 54 g (0.84mol) of sulfur dioxide were then introduced, and stirring at 50° C. wascontinued for 30 minutes. After cooling, 7.4 g (0.1 mol) of gaseouschlorine were introduced at room temperature, stirring was continued for15 minutes and the phases which formed were then separated. The organicphase was dried and the solvent was removed. This gave 207 g of methyl2-chlorosulfonyl-4-chlorobenzoate.

¹-NMR (CDCl₃, δ in ppm): 4.00 (s, 3H); 7.75 (m, 2H); 8.18 (m, 1H)

Methyl 2-mercapto-4-chlorobenzoate

Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder were addeda little at a time to a suspension of 205 g (0.75 mol) of methyl2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated hydrochloricacid and 375 g of ice. Stirring was continued for 3 hours, and themixture was then slowly heated to 70° C. After 2 hours at thistemperature, the mixture was cooled. The reaction mixture was allowed tostand at room temperature for 12 hours and then extracted with ethylacetate, the combined organic phases [lacuna] and the solvent wasremoved. This gave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.

¹H-NMR (CDCl₃, δ in ppm): 3.95 (s, 3H); 4.88 (s, 1H); 7.10 (m, 1H); 7.30(m, 1H); 7.96 (d, 1H).

Methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate

179.5 g (1.3 mol) of potassium carbonate and, a little at a time, 94.5 g(0.62 mol) of 3-bromopropionic acid were added to a solution of 125.4 g(0.62 mol) of methyl 2-mercapto-4-chlorobenzoate in 1.5 l of acetone,and the reaction mixture was stirred at room temperature for 12 hours.The solvent was distilled off, the residue was taken up in water and themixture was extracted with diethyl ether. The aqueous phase was thenmade acidic using concentrated hydrochloric acid and the precipitate wasfiltered off with suction and dried. This gave 160 g (88%) of methyl2-(2-hydroxycarbonyeth-1-yl)thio-4-chlorobenzoate M.p.: 133 to 136° C.

Methyl 5-chloro-4-oxothiochromane-8-carboxylate

At 70° C., 50 g (0.18 mol) of methyl2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate were against [sic] to500 g of polyphosphoric acid, and the mixture was stirred for 30minutes. The reaction mixture was subsequently added to water withstirring, and the resulting precipitate was filtered off with suctionand dried. This gave 41.1 g (88%) of methyl5-chloro-4-oxothiochromane-8-carboxylate.

¹H-NMR (CDCl₃, δ in ppm): 3.08 (m, 4H); 3.96 (s, 3H); 7.14 (d, 1H); 7.95(d, 1H).

Methyl5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate

30 g (0.078 mol) of methyl 5-chloro-4-oxothiochromane-8-carboxylate in300 ml of N,N-dimethylformamide dimethyl acetal were heated under refluxfor 6 hours. Volatile components were then distilled off, the residuewas taken up in methylene chloride and the organic phase was washed withwater. Drying and removal of the solvent gave 35.3 g (97%) of methyl5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate.

¹H-NMR (CDCl₃, δ in ppm): 3.18 (s, 6H); 3.80 (s, 2H); 3.95 (s, 3H); 7.24(d, 1H); 7.64 (s, 1H); 7.82 (d, 1H).

2-Methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol

1.3 g (29.2 mol) of methylhydrazine were added dropwise to a solution of7.0 g (22.5 mmol) of methyl5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylatein 700 ml of ethanol, and the mixture was heated under reflux for 2hours. The solvent was removed and the residue was chromatographed oversilica gel using the mobile phase ethyl acetate/cyclohexane (2:3). Thisgave 4.0 g (60%) of2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol.

¹H-NMR (CDCl₃, δ in ppm): 3.76 (s, 2H); 3.95 (s, 3H); 4.00 (s, 3H); 7.24(s, 1H); 7.36 (d, 1H); 7.70 (d, 1H).

2-Methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol

4.0 g (13.6 mmol) of2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol in100 ml of methanol/water (1:1) were refluxed for one hour with 0.8 g (20mmol) of sodium hydroxide. The organic solvent was removed under reducedpressure and the residue was extracted with ethyl acetate. The aqueousphase was acidified using concentrated hydrochloric acid and theresulting precipitate was filtered off with suction and dried. This gave3.5 g (92%) of2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol

¹H-NMR (CDCl₃, δ in ppm): 3.80 (s, 2H); 3.96 (s, 3H); 7.40 (d, 1H); 7.65(m, 2H).

In addition to the above compounds, tables 2 to 4 list further tricyclicbenzoylcyclohexanedione derivatives of the formula I which were preparedor are preparable in an analogous manner:

TABLE 2

Ia where m = O [sic], R¹, R², R⁵ = H, Y together with the two carbons towhich it is attached forms the following isoxazoline:

physical data (m.p. [° C.]; No. X R⁴ R¹⁰ R¹¹ R¹² R¹³ R¹⁴ R¹⁵ R¹⁶ ¹H-NMR[ppm]) 2.1 O OCH₃ OH CH₃ CH₃ ═O CH₃ CH₃ 7.42(d, 1H); 6.86 (d, 1H);4.62(s, 1H); 4.51(dd, 1H); 3.8-4.1 (m, 6H); 1.45(s, 12H) 2.2 O OCH₃ OH HH CH₃ CH₃ H H 206

TABLE 3

Ia where R₁, R², R⁵ = H, Y together with the two carbons to which it isattached forms the following substituted pyrazol:

physical data No. X R³ R⁴ R¹⁰ R¹¹ R¹² R¹³ R¹⁴ R¹⁵ R¹⁶ (m.p. [° C.]) 3.1S H Cl OH H H CH₃ CH₃ H H 124 3.2 S H Cl OH H H H H H H 127 3.3 S CH₃ ClOH H H H H H H 112 3.4 S CH₃ Cl OH H H CH₃ CH₃ H H 101 3.5 S CH₃ Cl OHCH₃ CH₃ ═O CH₃ CH₃  95 3.6 SO₂ CH₃ Cl OH H H H H H H 236 (decomp.) 3.7 SCH₃ —S—CH₃ OH H H H H H H 119 (decomp.) 3.8 S CH₃ —S—CH₃ OH CH₃ CH₃ ═OCH₃ CH₃ 212-214 3.9 SO₂ CH₃ —SO₂—CH₃ OH H H H H H H 277 (decomp.) 3.10SO₂ CH₂ —SO₂—CH₃ OH H H CH₃ CH₃ H H 251 (decomp.) 3.11 SO₂ CH₂ —SO₂—CH₃OH CH₃ CH₃ ═O CH₃ CH₃ 176 (decomp.)

TABLE 4

Ia where R¹, R², R⁵ = H, Y together with the two carbons to which it isattached forms the following methyl-substituted pyrimidine:

physical data No. X R⁴ R¹⁰ R¹¹ R¹² R¹³ R¹⁴ R¹⁵ R¹⁶ (m.p. [° C.]) 4.1 SCl OH CH₃ CH₃ ═O CH₃ CH₃  95 4.2 S Cl OH H H CH₃ CH₃ H H 100 4.3 S Cl OHH H H H H H 109

The compounds of the formula I and their agriculturally useful salts aresuitable, both in the form of isomer mixtures and in the form of thepure isomers, as herbicides. The herbicidal compositions comprisingcompounds of the formula I control vegetation on non-crop areas veryefficiently, especially at high rates of application. They act againstbroad-leaved weeds and grass weeds in crops such as wheat, rice, maize,soya and cotton without causing any significant damage to the cropplants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds of theformula I, or compositions comprising them, can additionally be employedin a further number of crop plants for eliminating undesirable plants.Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus cormnunis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which toleratethe action of herbicides owing to breeding, including geneticengineering methods.

The compounds of the formula I, or the compositions comprising them, canbe used for example in the form of ready-to-spray aqueous solutions,powders, suspensions, also highly-concentrated aqueous, oily or othersuspensions or dispersions, emulsions, oil dispersions, pastes, dusts,materials for spreading, or granules, by means of spraying, atomizing,dusting, spreading or pouring. The use forms depend on the intendedaims; in any case, they should guarantee the finest possibledistribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally active amount of atleast one compound of the formula I or an agriculturally useful salt ofI and auxiliaries conventionally used in the formulation of cropprotection agents.

Suitable inert auxiliaries are essentially:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.paraffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes or their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, e.g. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thetricyclic benzoylcyclohexanedione derivatives of the formula I, eitheras such or dissolved in an oil or solvent, can be homogenized in waterby means of a wetting agent, tackifier, dispersant or emulsifier.Alternatively, it is possible to prepare concentrates comprising activecompound, wetting agent, tackifier, dispersant or emulsifier and, ifdesired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, e.g. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acids, and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ether, condensates ofsulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene, or of the naphthalenesulfonic acids withphenol and formaldehyde,. polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds of the formula I in theready-to-use preparations can be varied within wide ranges. In general,the formulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight of at least one active compound. Theactive compounds are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

The formulation examples which follow illustrate the preparation of suchcompounds:

I. 20 parts by weight of the compound No. 3.1 are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 molof castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active compound.

II. 20 parts by weight of the compound No. 3.2 are dissolved in amixture composed of 40 parts by weight of cyclohexanone, 30 parts byweight of isobutanol, 20 parts by weight of the adduct of 7 mol ofethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of theadduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring thesolution into 100,000 parts by weight of water and finely distributingit therein gives an aqueous dispersion which comprises 0.02% by weightof the active compound.

III. 20 parts by weight of the active compound No. 3.4 are dissolved ina mixture composed of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the compound No. 3.5 are mixed thoroughly with3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts byweight of the sodium salt of a lignosulfonic acid from a sulfite wasteliquor and 60 parts by weight of pulverulent silica gel, and the mixtureis ground in a hammer mill. Finely distributing the mixture in 20,000parts by weight of water gives a spray mixture which comprises 0.1% byweight of the active compound.

V. 3 parts by weight of the compound No. 4.1 are mixed with 97 parts byweight of finely divided kaolin. This gives a dust which comprises 3% byweight of active compound.

VI. 20 parts by weight of the active compound No. 4.2 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 3.3 is dissolved in a mixturecomposed of 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. 4.2 is dissolved in a mixturecomposed of 80 parts by weight of cyclohexanone and 20 parts by weightof Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil).This gives a stable emulsion concentrate.

The active compounds of the formula I or the herbicidal compositions canbe applied pre- or post-emergence. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that they come into as little contactas possible, if any, with the leaves of the sensitive crop plants, whilethe active ingredients reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The rates of application of active compound I are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.

To widen the spectrum of action and to achieve synergistic effects, thetricyclic benzoylcyclohexanedione derivatives of the formula I may bemixed with a large number of representatives of other herbicidal orgrowth-regulating active ingredient groups and then appliedconcomitantly. Suitable components for mixtures are, for example,1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid andits derivatives, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoicacids and their derivatives, benzoic acid and its derivatives,benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl arylketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives,carbamates, quinolinecarboxylic acid and its derivatives,chloroacetanilides, cyclohexenone oxime ether derivatives, diazines,dichloropropionic acid and its derivatives, dihydrobenzofurans,dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers,dipyridyls, halocarboxylic acids and their derivatives, ureas,3-phenyluracils, imidazoles, imidazolinones,N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols,aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid andits derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formulaI, alone or in combination with other herbicides, in the form of amixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

USE EXAMPLES

The herbicidal activity of the tricyclic benzoylcyclohexanedionederivatives of the formula I was demonstrated by the followinggreenhouse experiments:

The culture containers used were plastic flowerpots containing loamysoil with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtranslucent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this has been adverselyaffected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to aplant height of 3 to 15 cm, depending on the plant habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. The test plants for this purpose were either sown directly andgrown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment. The rate of application for the post-emergence treatment was0.5, 0.25 or 0.125 kg/ha of a.s.

Depending on the species, the plants were kept at 10 to 25° C. or 20 to35° C. The test period extended over 2 to 4 weeks. During this time, theplants were tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

Scientific Name Common Name Abutilon theophrasti velvet leaf Chenopodiumalbum lambsquarters (goosefoot) Echinochloa crus-galli barnyard grassIpomoea ssp. morning glory Solanum nigrum black nightshade Sinapis albawhite mustard Setaria viridis green foxtail

At application rates of 0.25 or 0.125 kg/ha, the compound 2.1 exhibitsvery good post-emergence activity against the abovementioned undesirableplants Chenopodium album, Echinochloa crus-galli, Ipomoea ssp., Setariaviridis and Solanum nigrum. Furthermore, the compound 4.2, atapplication rates of 0.5 or 0.25 kg/ha applied by the post-emergencemethod, effects very efficient control of the harmful plants Abutilontheophrasti, Echinochloa crus-galli, Sinapis alba and Solanum nigrum.

We claim:
 1. A tricyclic benzoylcyclohexanedione derivative of theformula I

where: X is oxygen, sulfur, S═O, or S(═O)₂; Y together with the twocarbon atoms to which it is attached forms a saturated, partiallysaturated or unsaturated 5-membered heterocycle which contains one tothree identical or different heteroatoms selected from the followinggroup: oxygen, sulfur or nitrogen; R¹, R² are hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R³ is halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R⁴ ishydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁-C₆-alkyl)-aminosulfonyl,N,N-di-(C₁-C₆-alkyl)-aminosulfonyl, N—(C₁-C₆-alkylsulfonyl)-amino,N—(C₁-C₆-haloalkylsulfonyl)-amino,N—(C₁-C₆-alkyl)-N—(C₁-C₆-alkylsulfonyl)-amino orN—(C₁-C₆-alkyl)-N—(C₁-C₆-haloalkylsulfonyl)-amino; R⁵ is hydrogen,C₁-C₆-alkyl or halogen; m is 0, 1 or 2; R⁹ is a radical IIa or IIb

 where: R¹⁰ is hydroxyl, mercapto, halogen, OR¹⁷, SR¹⁷, SOR¹⁸, SO₂R¹⁸,OSO₂R¹⁸, NR¹⁹R²⁰ or N-bonded heterocyclyl which may be partially orfully halogenated and/or may carry one to three of the followingradicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; R¹¹, R¹⁵ are hydrogen, C₁-C₄-alkyl orC₁-C₄-alkoxycarbonyl; R¹², R¹⁴, R¹⁶ are hydrogen or C₁-C₄-alkyl; R¹³ ishydrogen, halogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,di-(C₁-C₆-alkoxy)methyl, (C₁-C₆-alkoxy)-(C₁-C₆-alkylthio)methyl,di-(C₁-C₆-alkylthio)methyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl; is 1,3-dioxolan-2-yl,1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl,1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six last-mentionedradicals may be substituted by one to three C₁-C₄-alkyl radicals; or R¹²and R¹³ or R¹³ and R¹⁶ together form a π-bond or a C₁-C₅-alkyl chainwhich may carry one to three radicals from the following group: halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; or R¹² andR¹⁶ together form a C₁-C₄-alkyl chain which may carry one to threeradicals from the following group: halogen, cyano, C₃-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxycarbonyl; R¹³ and R¹⁴ together form a—O—(CH₂)_(p)—O—, —O—(CH₂)_(p)—S—, —S—(CH₂)_(p)—S—, —O—(CH₂)_(q)— or—S—(CH₂)_(q)— chain which may be substituted by one to three radicalsfrom the following group: halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkylor C₁-C₄-alkoxycarbonyl; or R¹³ and R¹⁴ together with the carbon towhich they are attached form a carbonyl group; R¹⁷ is C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl,C₃-C₆-cycloalkyl, C₁-C₂₀-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl,C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl,C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl,N,N-di(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)-aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)-aminocarbonyl,N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)-aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)-aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)-aminocarbonyl, di-(C₁-C₆-alkyl)-aminothiocarbonyl,C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the alkyl, cycloalkyl or alkoxyradicals mentioned may be partially or fully halogenated and/or maycarry one to three of the following groups: cyano, C₁-C₄-alkoxy,C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl,hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl,di-(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy orC₃-C₆-cycloalkyl; is phenyl, phenyl-C₁-C₆-alkyl,phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl,phenoxythiocarbonyl, phenylaminocarbonyl,N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl,heterocyclyl, heterocyclyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonylor heterocyclyl-C₁-C₆-alkenylcarbonyl, where the phenyl or theheterocyclyl radical of the 18 last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹⁸ is C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl or C₃-C₆-cycloalkyl, where the four radicals mentioned maybe partially or fully halogenated and/or may carry one to three of thefollowing groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl; is phenyl,phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl, where thephenyl or the heterocyclyl radical of the four last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;R¹⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino,C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino,where the alkyl, cycloalkyl or alkoxy radicals mentioned may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals: cyano, C₁C₄-alkoxycarbonyl,C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl orC₃-C₆-cycloalkyl; is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl,heterocyclyl, heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, wherethe phenyl or heterocyclyl radical of the six last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²⁰ is hydrogen,C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl; p is 2, 3 or 4; q is 1, 2,3, 4 or 5; and their agriculturally useful salts.
 2. A process forpreparing compounds of the formula I where R¹⁰=halogen as claimed inclaim 1, which comprises reacting a tricyclic benzoylcyclohexanedionederivative of the formula Iα (=I where R¹⁰=hydroxyl),

where the variables R¹ to R⁵, R¹¹ to R¹⁶, X, Y and m are as defined inclaim 1 with a halogenating agent.
 3. A process for preparing compoundsof the formula I where R¹⁰=OR¹⁷, as claimed in claim 1, which comprisesreacting a tricyclic benzoylcyclohexanedione derivative of the formulaIα, (=I where R¹⁰=hydroxyl),

where the variables R¹ to R⁵, R¹¹ to R¹⁶, X, Y and m are as defined inclaim 1 with a compound of the formula IIIα or IIIβ L¹-R¹⁷ L¹-SO₂R¹⁸IIIα IIIβ

where the variables R¹⁷ and R¹⁸ are as defined in claim 1 and L¹ is anucleophilically replaceable leaving group.
 4. A process for preparingcompounds of the formula I where R¹⁰=R¹⁷, SR¹⁷, OSO₂R¹⁸, NR¹⁹R²⁰ orN-bonded heterocyclyl as claimed in claim 1, which comprises reacting acompound of the formula Iβ (≡I where R¹⁰=halogen),

where the variables R¹ to R⁵, R¹¹ to R¹⁶, X, Y and m are as defined inclaim 1 with a compound of the formula IVα, IVβ, IVγ, IVδ or IVβ [sic]H(N-bonded HOR¹⁷ HSR¹⁷ HOSO₂R¹⁸ HNR¹⁹R²⁰ heterocyclyl) IVα IVβ IVγ IVδIVε

where the variables R¹⁷ to R²⁰ are as defined in claim 1, if appropriatein the presence of an base.
 5. A process as preparing compounds of theformula I where R¹⁰=SOR¹⁸, SO₂R¹⁸ as claimed in claim 1, which comprisesreacting a compound of the formula Iγ (=I were R¹⁰=SR¹⁸),

where the variables R to R⁵, R¹¹ to R¹⁶ and R¹⁸, X, Y and m are definedas claim 1 with an oxidizing agent.
 6. A process for preparing tricyclicbenzoylcyclohexanedione derivatives of the formula Iα (=I whereR¹⁰=hydroxyl) as claimed in claim 1, which comprises acylating acyclohexanedione of the formula V in which the variables R¹¹ to R¹⁶ areas defined in claim 1,

with an activated tricyclic benzoic acid of the formula VIα or with atricyclic benzoic acid VIβ,

where the variables R¹ to R⁵, X, Y and m are as defined in claim 1 andL² is a nucleophilically replaceable leaving group and rearranging theacylation product, if appropriate in the presence of a catalyst.
 7. Acomposition, comprising a herbicidally effective amount of at least onetricyclic benzoylcyclohexanedione derivative of the formula I or anagriculturally useful salt of I as claimed in claim 1 and auxiliarieswhich are customarily used for formulating the crop protection agents.8. A process for preparing compositions as claimed in claim 7, whichcomprises mixing a herbicidally effective amount of at least onetricyclic benzoylcyclohexanedione derivative of the formula I or anagriculturally useful salt of I and auxiliaries which are customarilyused for formulating crop protection agents.
 9. A method for controllingundesirable vegetation, which comprises allowing a herbicidallyeffective amount of at least one tricyclic benzoylcyclohexanedionederivative of the formula I or an agriculturally useful salt of I asclaimed in claim 1 to act on plants, their habitat and/or on seed.